PL128500B1 - Herbicide and process for manufacturing o-alkylsulfonyloxy and o-alkylsulfonylamino-benzenesulfonamides - Google Patents

Description

The subject of the invention is a herbicidal agent containing as active substances o-alkylsulfonyloxy and o-alkylpsulfonylamino-benzenesulfonamides. Dutch Patent No. 121788 describes the preparation of compounds of formula 1, used as general or selectively acting herbicides. of general formula I, Rx and R2, each independently represent an alkyl group of 1-4 carbon atoms and R and R4, each independently represent a hydrogen atom or an alkyl group of 1-4 carbon atoms. in which R is a pyridyl group are described in J. Drug. Res. 6,123 (1974). Their use is known as anti-diabetic agents. U.S. Patent No. 4,127,405 discloses compounds of the general formula (III) in which R 0- represents the group represented by the formula 4, 5 and 6 or the group α- naphthyl, and Rs and R ", each independently represent hydrogen, fluorine, chlorine, bromine, alkyl, 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, nitro, trifluoromethyl, cyano, or a group of the formula ... CHiS (O) n or of the formula CHiCH ^ (OJn, R * represents a hydrogen, fluorine, chlorine, bromine atom or a methyl group, R5 represents a hydrogen, fluorine, chlorine, bromine atom, methoxy or methoxy group, R7 is hydrogen, fluorine, chlorine, bromine, alkyl group with 1-2 carbon atoms or alkoxy group with 1-2 carbon atoms, R8 is hydrogen atom, methyl group, chlorine atom or bromine, R9 and Ri0 each independently represent a hydrogen atom, a methyl group, a chlorine or bromine atom, W and Q each independently represent an oxygen or sulfur atom, n is 0.1 or 2, X is A hydrogen, chlorine, bromine atom, a methyl, ethyl, alkoxy group with 1-3 carbon atoms, a trifluoromethyl group, a group of the formula CHgS- or of the formula CH3OCH2-, and Y is a methyl or methoxy group, and ) when R5 is not hydrogen, at least one of Rj, R4, B + and R7 is not hydrogen, and at least two of R8, R *, R "and R7 'are hydrogen, b) when R5 is hydrogen and when all R & R4, R * R7 are other than hydrogen, then * each of Ra, R4, R8 and Ry are chloro or methyl groups, and c) when R And R7 are hydrogen, at least one of R4, R5, or R1 is a hydrogen atom and their agriculturally useful salts. 20 25 30 The discussed patent specification provides information on compounds substituted in the ortho position, in which the substituent is an alkyl group with 1-4 carbon atoms. In commercial crops, the development of undesirable 128 5003 plants causes significant losses, especially in agricultural products necessary to provide basic human nutrition, such as soybean; corn, wheat and the like. The current population growth and the accompanying global lack of austerity require an improvement in the efficiency and production of these crops. One way to improve productivity is to prevent or minimize the loss of valuable crops by destroying or restraining the growth of some unwanted plants. A wide variety of substances are known and available that are useful in destroying or preventing undesirable plants from growing. These substances are generally called herbicides. However, there is still a need for more effective herbicides that destroy or delay weed growth without causing significant damage to crop crops. 2o An agricultural herbicide that kills weeds in general or selectively pre- or post-emergence according to the invention as active ingredient is a compound of formula 7, wherein Q is oxygen or a group of formula NR5, Ri is an alkyl group with 1-4 carbon atoms, a trifluoromethyl group or a phenyl group, Rf is a hydrogen or chlorine atom, or a methyl group, Rj is a hydrogen or chlorine atom, R4 is a hydrogen atom or a methyl group, R5 is a methyl group, X is a group of the formula Npe alkyl with 1-2 carbon atoms, a methoxy group, an alkenyloxy group of the formula OCH2CH = CHj or a group of the formula OCH2CF5, Y is a hydrogen atom or a chlorine atom, a methyl group or a group of methoxy and Z is methyno CH, nitrogen or a group of formula CCl, where when Y is chloro, Z is different from nitrogen and X is NHCH ', or methoxy when Y represents a hydrogen atom and X represents a met group lead and Z are different from nitrogen. Preferred because of their higher herbicidal activity and / or easier, more preferred synthesis are: (a) Among the group of compounds of general formula 7 above, a preferred group is those in which R x is an alkyl group of 1-450 carbon atoms or a trifluoromethyl group. (b) Among the group of compounds (a), a preferred group is those in which Rj is hydrogen. (c) Among the group of compounds (b), a preferred group 55 are those in which Rf is hydrogen. (d) Among the group of compounds (c), a preferred group are those in which R x is an alkyl group of 1-3 carbon atoms or a trifluoromethyl group, Q is an oxygen atom and Z is a methine group or a nitrogen atom. (e) Among the group of compounds (d), a preferred group are those in which R 4 is carbon atom (f) Among the group of compounds (e), a preferred group are those in which X and Y are each independently methyl. or methoxy and R 1 is methyl. Particularly preferred for their highest herbicidal activity and / or the most advantageous and simple synthesis are: N 1 -H, 6-dimethyloxypyrimididine-2-yl (aminocarbonyl) -2 methylsulfonate -hydroxybenzenesulfonamide, 2-hydroxy-N - (- H-methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl) -benzenesulfonamide methylsulfonate, and N - (-) 4,6-dimethylpyrimidine-2-yl methylsulfonate N- (-) 4,6-dimethoxy-1,3,5-triazin-2-yl) -aninocarboxyl (-2-) methylsulfonate of N- (-) 4,6-dimethoxy-1,3,5-triazin-2-yl) -anino-carbonyl. hydroxybenzenesulfonamide, 2-hydroxy-N - (-) 4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl) -benzenesulfonamide methylsulfonate, methylsulfonyl n N - (-) 4,6-dimethyl-1,3,5-triazino-2-yl) -aminocarbonyl) -2-hydroxybenzenesulfonamide, N4 (-) 4,6-dimethoxy-1,3-methylsulfonate , 5-triazin-2-yl (methyl) aminocarbonyl) -2-hydroxybenzenesulfonamide, and N- (-) 4,6-dimethoxypyrinyl-1-propylsulfonate-N- (-) 4,6-dimethoxypyrinyl-N-carbonyl (2-hydroxybenzenesulfonamide) showing selectivity in rice and corn, as well as 2-hydroxy-N - (-) 4-non-toxic-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl / benzenesulfonamide 1-propylsulfonate, which act selectively in The method of producing new compounds of the general formula 7, in which Q, Rlf R *, R3, R4, X, Y and Z have the above meaning, according to the invention, it consists in the fact that the compound of formula general 8 in which Q, Rlf Rj and Rl The above meanings are reacted with a compound of general formula 9 in which R 4, X, Y and Z are as defined above. The reactions are preferably carried out in an inert solvent such as methylene chloride or acetonitrile. The method of carrying out the reactants is not critical, but it is usually preferred that an isocyanate or thioisocyanate solution of general formula 8 is added to the stirred suspension of a heterocyclic amine of general formula 9. The reaction is essentially exothermic. In some cases, the desired product does not dissolve in the reaction medium and crystallize out in pure form. On the other hand, the products soluble in the reaction medium are isolated by evaporating the solvent and triturating the residue with solvents such as diethyl ether, 1-chlorobutane or hexane, and then filtering. Q represents an oxygen atom or a group of formula NR5, Rx represents an alkyl group of 1-4 carbon atoms, a trifluoromethyl group or a phenyl group, R2 represents a hydrogen or chlorine atom, or a methyl group, R | represents a hydrogen atom or a chlorine atom, R5 represents a methyl group. Preferred starting compounds used in the process of the invention are because of the favorable and simpler course of the synthesis and / or leading to the formation of the compounds of the formula VII with a preferred intensity. herbicidal activity are: compounds of formula 8 in which Q is oxygen, Rj and R 'are hydrogen, Rx is methyl or trifluoromethyl, and compounds of formula 13 in which Q is NCHt, R2 and R 1 represents hydrogen and R 1 represents a methyl or trifluoromethyl group. Preferred intermediates for the preparation of the herbicidal compounds of formula VII are compounds of formula 10 in which Q is oxygen or the group of formula NR5, Ri is an alkyl group with 1-4 carbon atoms, a trifluoromethyl group or a phenyl group, Rf is a hydrogen or chlorine atom, or a methyl group, Rj is a hydrogen or chlorine atom, R5 is a methyl group and Z is and a methino group CH or a nitrogen atom. The method according to the invention is illustrated by schemes 1-2 in the accompanying drawings. Thus, the compounds of formula VII and 12 can be obtained by reacting the corresponding 2-amnopyrimidine of formula 9 or the 2-aiminotriazine of formula 11 with the correspondingly substituted sulfonylizateanates of formula VIII, wherein in the formulas Q, R1f, R2, R * , R4, X, Y and Z have the meaning defined previously. The intermediates of formula 10 are obtained by reacting a sulfonamide of formula 14 with 4,4-cfvchloroheterocyclic isocyanates of formula 13. This is illustrated in Scheme 3 in the accompanying figures. One or both of the halogen atoms in the heterocyclic ring of a compound of Formula 10 may be replaced with an alcohol moiety of Formula CR6 to give a compound of Formula 15 wherein R5 is an alkyl group of 1-2 carbon atoms, alkenyl of Formula CH * —CH = CH2 or a group of formula CH * CFS, and Y is a chlorine atom or a methoxyl group, according to Scheme 4 in the accompanying figures. The preparation of compounds of formula 15 is described in South African Patent No. 80 / 607,457. .Sulfonamides obtained method op Sana in Reearch Disclosura, p. 52 (1978), can be readily converted to the corresponding isocyanates of Formula 8 according to the method described in US Patent No. 4,127,405. An overview of the synthesis of heterocyclic amine derivatives is given in the serial Interscience Publ. New York, London - "The Chemistry of Heterocyclic Compounds", where DJ Brown in "The Pyrimidines" Vol. XVI describes 2-aminopyrimidines. The preparation of the amino-dicyclopyrimidines is described in Unexamined European Patent Specification No. 15,683. Heterocyclic amine the intermediates of formula 9 and 11 in which R 4 is a methyl group can be obtained as illustrated in Scheme 5, or by an obvious modification of the method illustrated in Scheme 5. A solution of the amine of formula 16 in concentrated hydrochloric acid is contacted with aqueous solution of sodium nitrite and the resulting chlorine compound of formula 17 are separated from the acid solution by filtration (see, for example, Bos and Rose J. Chem. Soc. C, 2051 (1966) for the case where Z is methyne and X and Y are methoxy). The exchange of the chlorine atom can be accomplished by heating with an excess of methylamine in a water environment to obtain a methylamino-heterocyclic compound of formula 18. The herbicide according to the invention containing a compound of formula 7 as active substance is prepared in a manner conventional. The composition of the invention may be in the form of a powder (dustable), granules, tablets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. A number of them can be used directly. The sprayable formulation according to the invention may be distributed in suitable media and used in volumes ranging from a few liters to hundreds of liters per hectare. Compositions with a high concentration of active ingredient are in principle used mainly as intermediates for the preparation of further formulations of the agent according to the invention. These compositions contain from about 0.1 to 99% by weight of the active ingredient and at least one additional ingredient such as (a) a surfactant in an amount of from about 0.1 to 20% and (b) a solid or liquid diluent in an amount of from about 0.1 to 99.9%. The composition of the present invention is shown in the following table 1. The form of the agent of the present invention is moistened with powders, slurry in paste, emulsion, solutions (including emulsion concentrates), aqueous suspensions, powders, granules and tablets. at the concentration of Abel 1 in Active substance 20-90 3-50 10-50 1-25 0.1-95 90-99 Content of 1 by weight * Diluent 0-74 40-95 40-84 70 —99 5—99.9 0—10 1 Surfactant 1—10 0—15 1—20 0—5 0—15 0—2 * Active substance + at least one of the surfactants or diluents —100% By weight, the herbicide according to the invention may, of course, contain more or less active ingredient, depending on the intended method of application and the physical properties of the compound. Sometimes a higher ratio of surfactant to active substance in the composition of the invention is required, achieved by incorporation into the formulation or by mixing the formulation in a working tank with additional amounts of surfactant. pdwe r # i fitnfi fit al "Mtódbook of Insecticide, Dusi, Diluents ihd Carriers" - second edition of Dorland Books, Catowelil New Ifefsey, but in the middle of the invention, other natural or synthetic steels may also be used. For wet powders, diluents with stronger absorptive properties are preferred, while for powders - diluents with higher density. 1 sheet) in liquid diluents and solvents are described in Mardden Soivents Guide - Second Edition, New York 1950. For suspension concentrates, a solubility of less than 0.1% has been used. phase separation at 0 ° CW "Me Cutcheoh's Detergens and Emulsifiers Annual" MC friblfehing Cbip., Eidgewood, Ney Yersey as fowhlez S. Bidy and Wood "Ericyclogedie 0f Surface Active AgfemV 'Chemical ihiblishihg Ccl, Inc., New Ydfrft, 1 $ 64 According to the present invention, the liquid and liquid surfactants of the surfactant and the surfactants may additionally contain small amounts of adjuvants to reduce the propensity. for foam, caking, corrosion and growth of microorganisms, etc. The methods for making such compositions are quite suitable. The solutions are prepared by slowly mixing the ingredients. Fine-grained compositions are constantly prepared by mixing and usually grinding them either in milk mills or in fluidized mills. Suspensions are prepared by "wet" milling (see U.S. Patent No. 3,060,084). Granules and pellets can be prepared by spraying the active material into pre-formed granular potties or by using these methods. agglomeration (see JB Browning "Agglomeration *, Chemical Engineering Dec 4, 1967 p. 147 ff and" Perry ^ Chemical Engoiueer ^ s Haitolbook ", fifth edition, Mc Graw-Hill, New York, 1973, pp. 8- ^ 57 ff). Further information on how to formulate various forms of herbicides can be found in: United States Patent No. 3,235,381, United States Patent No. 3,309,192, United States Patent No. 2,891,855, GCKlinoman Publication , "Weed Control as a Science," John Wiley W. Sohs inc. New York, 1961, pp. 81-96 and in JD Freyer and SA Evan's "Weed Con- Iról Handbook" fifth edition Blackwell Science PtiblicatiOHS, Oxford 1968, pp. 101-103. herbicidally active, They find a wide range of uses for pre-emergence and / or post-emergence weed control in areas where it is desirable: it is complete control of all wets (JJi (plants) in places such as: for fuel storage tanks, ammunition depots, industrial areas, places for oil wells, theater squares for motorists, places around advertising boards, structures, highways and railroads. Compounds manufactured according to the invention can also be used with good effect for modifying plant growth and for selectively controlling weeds in crops such as wheat, rice, maize, soybean and barley, with the correct choice of dose, time and method of application, The application rates of the active ingredient used in a given situation vary depending on the intended desired effect of the application, the amount of greenery at the time of application of the active ingredient, the types of weeds to be controlled, the types of crops desired at the application site active ingredient, soil type, form of herbicide, method of application, weather conditions and the like. Since so many variable parameters play a role, it is not possible to set a single dose for all situations. In general, the compounds produced according to the invention are applied at rates of from about 0.001 to 20 kg / ha, preferably from 0.01 to 10 kg / ha; In general, higher doses within the said range will be selected under unfavorable conditions or when a longer residence time in the soil is desired. The compounds of the invention of Formula 7 may be combined with other herbicides and are particularly useful in combination with ureas such as: 3- (3,4-dichlorophenyl) -1,1-dimethylurea, with triazines such as 2-chloro-4- (ethylamino) -6- (isopropylamino) -s-triazine, uracils such as 5-bromo -3-IIt-butyl-6-methyluracil (bromacil), N- (phosphonomethyl) -glycine, 3-cyclohexyl-1H-methyl-6-dimethylamino-35 -s-ltriazine-2.4 <1H, 3H) -dioiL,, N, CHDivinethyl-2,2-diphenylacetamide, 2,4-dichlorophenoxyacetic acid (2,4-D) and similar compounds, 4-chloro-2-butynyl-3-chlorophenyl carbamates, S- (2,3- -dichloroallyl (-diisapropylthiocarbamates, iq S -. (2,3,3-trichloroallriIoMmiumetyl), 5 ^ in \ ife (nyl-1Hnpyraisolyl methyl sulphate, 2- (4- / 2,4HdichlorofeoKolxy / -phenoxy) -propianiLan me tyl, 4-amino-6-tert-butyl-3-rophenyl) -1-methoxy-1-methyl-urea, 3-isopropyl-4H-2, 1,3-dioxide -4 (3H) -one, alpha-alfanalia, trifluoroix-2,6-diiiiitiro-N ^^ dipropyl-p-toluidine, 1,1 '^ dimethyl-4,4'-bipyridinium ion, monosodium methanarsenate, acetanilide 50 2-chloro-2 ', 6'-diethyl (methoxymethyl), 1,1-dimethyl-3 ^ a, a, a-trifluoro-m-tolyl) -urea and 5- (2-chloro acid methyl ester) -4 - /) trifluoromethyl / phenoxy) -2-nitrobenzoic acid. The activity of these compounds was tested in greenhouse tests. Description of the tests carried out. and their results are given below. .Test A. Seeds of bloody finger - Digitaria spp. Unilateral weed - Echinochloa crusgallif. gluchego oats -r- Avena fatus, 60 Cassia - Cassia tora, morning glory - Ipomoea sp. sorghum - Xanthium spp. sorghum, corn, soybean, rice, wheat and sand sedge - Cyperus rotundus was planted in growth medium and treated before the emergence of the plants, the test compounds gj dissolved in the compound solution produces • t IM SM l of the herbicidal agent. The pre-and post-harvest treated plants and controls were kept in the greenhouse for sixteen days, then the treated samples were compared with their respective controls and the treatment results were visually evaluated. Stopped aastepl * - what rating system: 0 - no effect 10 - maximum effect C - bland or dieback D - leaf loss E - inhibition of germination G - growth retardation H - shape effects B - unusual pigmentation GY - attacked (cut) parcels or flowers P - destruction of growth bundles S - burning hang deaf rice trachea one-sided finger, bloody bindworm, sandworm, icassia and sand turkey Compound of formula 19 0.05 4C, 9G, 6Y fiC, 2G 2C, 9G 8G) IC, 8H IC 2C, 8G SC, 9G 5C, 9H 3C, 7H 6C, 9G 6C, 9G ac, 6H 5C, 9H 3C, 9H 2C, 8G 2C, 2H 0 3C, 8H 4C, 8H 3C, 7H IC, 5G 3C, 9H 2C, 8H 5C: 10E Compound of formula 20 0.05 9C 6C , AG 5C, 9G 8C, 19H 3 5C, UG 1 • IC 3C, 9G 5C, 9G 9C 4C, 9H 9C 9C 5C, 9H 10C 10H 9G 9H 5G 3C, 9H 5 C, 9H 6C, 9H 3C, 8H 2C, 9H 9H 3C, 9G ¦ME: Compound of formula 21 r 0.05 9C SC, 9H 8U, 9G 5U, 9G 9C IC 2C, 9G 5C, 9G «C, 9H 9C 7C, 9G 9C 5C, 9G 9C 3C, 9H 9G 9H 9 9H 10E 4C, 9H 2C, 8G 2H, 9G 9H 5C, 9G 1 10E 1 Compound of formula 22 -., _ - | '.. - .- .: • -. . i \ t), 05 4C, 8G, 6Y 1 3C 2C, 9H 3Q * 9H 2C, 6G, 5X -e 2C, TO * j 2C, 8G, 6X | 2C, 8H i 0 J 3C, 8fi \ IC, 4G i IC, 3G J 3G J iii I 1C 1 IC, 3G I m 1 0 i 3G] IC] 2C] 0 i IC i 0 1 IC] 0 i 1 the method according to the invention of Table 2 in a mephitotoxic solvent. At the same time, a solution of the compound from Table 2 in a non-phytotoxic solvent was sprayed, cotton with 5 leaves (including leaves), climbing beans with a three-foil leaf, bloody stick and one-sided weeds, crabgrass and pranyard grass with 2 leaves, deaf oats with 2 leaves, cassia (Cassia toraj with 3 leaves (including leaves), bindweed and turnip with 4 leaves (including leaves), sorghum and corn with 4 leaves, soybeans with 2 leaves, reams with 3 leaves, wheat with 1 leaf and sand sedge (Cyperus) with 3-5 leaflets In order to carry out a solvent control, the above-mentioned weeds and crops placed in other tanks were treated before or after emergence with the same non-phytoxic solvent. subjected to ob-128 500 11 12 Table la Dose kg / ha After plant emergence cotton beans sorghum 1 corn soybean wheat oat deaf rice weed weed one-sided bloody p seaweed 1 porridge 1 cassia sand sedge Pre-emergence of plants sorghum maize soybean wheat and oats deaf rice weed weed one-sided bloody stalk 1 two-sided turnip cassia sand sedge Compound of formula 23 [M * 9C 6C, 9G 1 9C 9C 9C 2U, 9G 3C, 9G, 6G 6 9C 9C 4C, 9H 4C, 9H 5C, 7H 2C, 4G 10H 3C, 9G 5C, 5H 1C 3C 9H 3C, 9H 1C 4C, 9H - 3C, 3H 1C | Compound of formula 24 9C 6C, 9G 9C 7U, 9G 4C, 9G 2C 2C, 4G 5C, 9G 5C, 8H 3C, 9G 4C, 9H 4C, 9G 4C, 6H 3G, 5X 5C, 9H 2C, 9G 2C, 5H 2C 2C, 5G 9H 3C, 9H 1C 2C, 9G 9H 2C, 3H 3G 1 Compound of formula 25 0J05 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 0 | Compound of formula 26 0J05 3C, 3H, 5Y 2C, 2H 2C, 4G 1C, 5H 2C, 6H 0 0 4G 2C, 4H 0 3C, 7H 3C, 9G 3C 8G 2C, 6G 3C, 7G 1C 0 0 1C, 3G 2C , 8H1C | 6H, 2C 3C, 8H 1C 1C, 8G | Table Ib Dose kg / ha [After plant emergence cotton beans sorghum maize soybean wheat oats deaf rice weed weed bloody morning glory turnip 1 Cassia sand sedge 1 Before plant emergence sorghum maize soybean wheat oats deaf rice weed sorghum with formula 27 | 5 ~ 4C, 9G, 6Y 4C, 7H 1C, 3G 1C 2C, 8H 0 0 4G 2H 0 3C, 8G 4C, 9G 1C, 3G 1C, 8G 1C, 4G 1C, 4G 1C 0 and 0 1C, 4G 3C 1C 8G , 2C - 0 9G 1 Compound of formula 28 | 0 ^ 05 1C 1C, 2G 0 0 1H 0 0 0 0 0 2C, 7H 4G 1C 0 0 1C, 5G 1H 0 0 2G 2C 0 0 0 0 o 1 Compound of formula 29 | 3C, 9G, 6Y 2C, 6G 2C, 9H 3U, 9G 3C, 9G 0 0 1C, 6G 4H 0 3C, 9G 3C, 9H 0 0 1C, 4G 3C, 7G 1C 0 0 1C, 3G 1C 0 8H, 2C __ 0 o 1 Compound 1 of formula 30 0 ^ 5 9G 6C, 9G 2G 0 2C, 8H 0 0 0 0 0 6C, 9G 9C 5C, 8G 0 4G 0 0 1 € I 0 2G 2C 0 9C 9H | 5C, 9G j 5G128 509 13 14 0) Xi cd * - * • * sa cd- fc o cd xi * i— Dose kg lO o sciu plants • 1-9 O Cu H CD OOWW «O) O) 10 o ~ o "1 o ~ co no cd cd d 3% cd 2« W, Q cg o org c / 3 00 os o ~ o ~ CN cd ¦u M 1 M 3 ICO cd w OO ii uchy 2 w szeni wies po owoo co o "CN • N ^ H m U CN cd ddo fi ica unit sa £ ^ o CN o ~ rH k bloody Id p OJ U io -oop OO) ^ d CU zep u OO) 3" cd • i— » cont. «O co sandwich cd o - * j OO) jkrowa o urak Xi a descent ro fc * c N In On ffi ffi 00 00 u" oo ~ tu N CO ^ cd N T3 o SW) ^ cd o R o Vi X vx lH cont. D ee ear W) wies o 0 O and co OO) OO) o "uoo tu o" oo * CM 10 cd § O u ica unit fl co cd »Xi» HO CN O) k bloody 6 " ii £ cd o D, Cu O) <3 CU zep ii lO cd • r- »Vi cd ^ d Tfl 10 O sand roe Cd ° * 3 3 * 43. O» ss s * N o * sas ^ "^ OO) N f88 N o ^ o 0.4 0.05 cont .d UJ cont. Cont. 1 o After plant emergence O From ffi OO what O) O) OO "O" 13 O OJ OO) o beans ¦ «* O ol — 1 o cotton CN lO OE OJ OJ CC o sorghum CN o maize O) O Ol o cd 'cl Vi oo OO) o ~ c ooo 00 OJ oo * o ~ CN * - • OO wheat deaf sheep what o O what o ~ iH o oj WO t- oo ~ oo ~ ^ CO OJ ffi OO OJ o ~ 10 o rice one-sided weed ^ CO OJ o ~ o 'oo CN CO O lH o CN o "O iH O fingers bloody bindweed turnip OJ kas ja HO 0 ~ CN O 00 U CN O sand sedge Before plant emergence OO ffi OO OJ u lO OJ 00 00 U 0 ~ O CN ffi O OJ o "lO o sorghum ^ CN 00 o ~ CN O OJ 00 t" MOU CN O corn OJ o soybean 00 O wheat - ^ O deaf sheep W iH W o tH OOO OJ o "^ K OJ o ~ ^ o rice weed one-sided «tf o" i-i O r- OEO ~ 0 OJ OJ CO 00 oo O) OJ oo W o ~ u "ir: o bloody finger Oi o bindweed Oi TT iH OOO turnip cash i sand sedge 128 500 15 16 Table 2 Dose kg / ha. After plant emergence, cotton bean, morning glory, cassia, sand sedge, bloody weed, one-sided, oat, deaf, wheat, corn, soybean. rice sorghum Pre-emergence morning glory turnip cassia sand sedge bloody weed one-sided oat deaf wheat and corn 'soybean rice | sorghum Compound of formula 32 0.1 9C 10C 10C 10C 9C 9C 9C 10C 2C, 9G IC, 2G 5C, 9G 9C 9C 9C 9G 9H 9C 10E 9C 5C, 9H 1U, 9G 5G 2U, 9G v 9H 10E 7C, 9H Compound of formula 33 0.1 9C 9C 10C 10C 9C 9C 9C 10C 4C, 9G 5C, 9G 9C 9C 9C 10C 9G 1 9H 5C , 9G 10E 6C, 9G 9C 5C, 9H 5C, 9H 1 10E 9H 10E 6C, 9H Compound of formula 34 0.1 9C 10C 10C 9C 9C 9C 9C 10C 5C, 9G 5C, 9G 9C 9C 9C 9C 9C 9H 6C, 9G 10E 2C, 8G 3C, 9H ¦ 4C, 9H IC, 9H 10E 9H 10E 10H Compound 1 of formula 35 1 0.1 9C 9C 10C 10C 9C IC, 5G 4C, 9G 4C, 9H 40, 9H 0 4U, 9G 9C 9C 2C, 9H 9C 9H € C, 9G IC, 7G 2C, 5G 7C, 9H 8G 3G 3C, 9H 9H 10E IC, 9G | Table 2a Dose kg / ha. Post-emergence Cotton bean Morning glory cassia sand sedge bloody weed one-sided oat deaf wheat maize soybean rice | sorghum Compound of formula 36 0.1 9C 9C 10C 9C 9C 5G 2C, 9G 5C, 9H IC, 4G 0 6C, 9G 9C 9C 2C, 9H Compound of formula 37 0.1 9C 9C 10C 9C 6C, 9G IC, 5G 9C 9C 3C, 9G IC 6C, 9H 9C 9C 6C, 9G Compound of Formula 38 1 0.1 IC, 2G 9C 9C 9C 5C, 9G 2C, 5G 3G 0 0 0 3C, 9H 9C 6G IC, 3G] Pre-emergence. plant morning glory turnips | cassia sand sedge stalk blood weed weed one-sided oat deaf wheat maize soybean rice 1 sorghum 9C 9H 6C, 9G IC, 6G 2C, 6G 2C, 9H IC, 7G 0 9H 9H 10E 5C, 9H 6C 9H 6C, 9G 6G IC, 6G 7C, 9H 3C, 9G 8G 9H 9H 10E 7C, 9H IC, 3G 8H 2C, 2H 0 0 0 0 0 3G IC, 2H 1 IC 0 1 25 128 500 18 Table 2b Dose kg / ha E After plant emergence cotton beans sorghum I soybeans 1 wheat oats deaf rice one-sided weed weed 1sided swarm 1kassia sand sedge Before plant emergence sorghum maize soybean wheat oats deaf rice one-sided weedworm bloody bindworm turnip 1kassja | sand sedge Compound of formula 39 0fi5 10G, 9C 10G, 9C 10G, 4C 10G, 7C 0 0 8G, 3C 10G, 6C 0 10G, 9C 10G, 9C 10C 10G, 7C 8G, 5G 6G 8G, 5H 0 5G, 3H 8G , 6C 8G, 5H 3G 8G, 5C 8G, 3H 9G, 5C 10E Compound of formula 40 0fi5 9G, 3H, 6C 10G, 8C 10C 10G, 8C 3C, 2C 9G, 3C 10C 10C 8G, 3C 7G, 9C 10C 10G, 8C 10G, 6C 9G, 9C 9G 9G, 5H 7G 8G, 3C 8G, 8C 9G, 6C 5G, 3H 8G, 9C 9G, 9F 9G, 9C 10E Compound of formula 41 0fi5 7G, 3H, 7C 10G, 8C 10G, 9C 7G, 7C 3G, 2C 10G, 6C 10C 10G, 9C 0 10G, 5C 10G, 7C 10G, 8C 10G, 7C 9G, 9C 9G, 9C 8G, 5C 7G 7G, 5H 10E 8G, 5H 3G 8G, 9C 9G, 9P 8C, 9G 10E Compound 1 of formula 42 0 ^ 05 2C, 2H 3C, 2H, 6G 0 2H, 6G 0 0 IC 2H 0 9C 3C, 9G 0 0 0 0 0 0 0 3G 0 0 7G 5H 0 0 | Table 2c Dose kg / ha | After plant emergence and cotton beans sorghum maize soybean I wheat oats deaf rice weedweed one-sided bloodworm morning glory cassia sand sedge sugar beet Before plant emergence sorghum maize soybean wheat oat deaf rice weed sorghum soybean sand sugar beet I Compound of formula 43 M5 IC, 2H IC 6H 0 and 1H 0 0 0 0 0 IC, 5G IC 0 - 0 0 0 0 0 0 0 0 0 0 0 0 - Compound of formula 44 GC, 9G, 6Y 3C, 3H, 9G 0 0 2H, 6G 0 0 0 0 0 4C, 5H 4C, 9H 3C - 0 0 0 0 0 0 0 0 3C, 9G 8H, 3C 2C 0 - Compound of formula 45 0 ^ 05 6C, 9G , 6Y 3C, 3H, 9G 0 0 2H, 5G 0 0 0 0 0 3C, 9H 2C, 8G IC - 0 0 0 0 0 0 0 0 4C, 9G 7H, 3C 0 0 - Compound and formula 46 5 8G, 7C 7G, 2C 7G 3G 6G, 5H 0 0 5G 2G 0 7G 9G, 9C 2G 8G 8G, 5H 5G 4G, 3C 2G 3G 7G 5G 0 9G 9G and 8G 10C 9G, 9C | 128 500 19 26 Table 2d Dose kg / ha After plant emergence, cotton beans sorghum _ corn soybean wheat oat deaf rice weed weed one-sided stick bloody morning glory turnips en cassia sand sedge Before plant emergence sorghum maize soybean wheat oats deaf [rice Ich 0 0 0 0 0 0 0 0 Compound of formula 48 Qfi5 3C, 9G, 6Y 7C, 6G 3C, 4G 4C, 3U, 4G 6C, 7G 0 2C 2C, 3G 10C 2C, 3G 10C 10C 8C, 7G 10C 3C, 6G 3C, 6G 7C, 8G 0 2C 10E 7C, 8G 2C, 2G 7C, 7G 8C, 7G 8C, 8G 10E Compound of formula 49 OfiZ 9C, 7G 8C, 7G 2C, 4G 5C, 6G 10C 0 3C, 4G 3C, 4G 7C, 6G 0 5C, 4G 8C, 7G 3C, 4G 6C, 4G 5C, 8G 7C, 6G 7C, 8G 3C, 5G 7C, 6G 8C, 8G 7C, 7G 3G, 2C 10C 3C, 5G 7C, 6G 10E Compound 1 Formula 50 OC 05 6C, 7G. 6Y 9C, 6G 2C, 4G 0 7C, 8G 2C, 2G 3G 1 3C, 5G f 2C, 3G 0 10C 10C 3C, 4G 5C, 4G 7C, 7G 0 7C, 6G 0 2C, 6G 8C, 7G 7C, 5G 0 7C, 6G 5C, 6G 5C, 4G 10E Table 2e Dose kg / ha Post-emergence cotton beans' sorghum maize soybean wheat oats deaf, rice weed weeds bloody morning glory cassia 1 sands sedge I Before plant emergence I Sorghum | maize soybean [wheat oat deaf [rice weed weed 1 sided scabbard 1 bindweed 1 cassia [sand sedge Compound of formula 51 Qfi5 2G 5C, 4G 4C, 5G 10C 4C, 5G 0 4C, 5G 3C, 4G 7C, 6G 2C, 2G 10C 10C 2C 0 7C, 8G 7C, 8G 6C, 7G 0 2C, 5G 10E 7C, 7G 4C, 5G 10C 10C 5G, 6C 1 ° Compound of formula 52 9C, 6G, 6Y 9C, 5G 6C, 5G 7C, 6G 5C, 6G 2C, 3G 8C, 7G 2C, 3GL 10C 7C, 6G 10C 10C 5C, 3G 3C, 4G 7C, 8G 8C, 8G 7C, 6G 0 5C, 6G 10E 8C, 8G 5C, 7G 10C 10C 7C, 6G 7C, 5G Compound of formula 53 M and 3C, 4G, 6Y 0 0 0 0 0 0 0 0 0 [° 6 0 0 0 0 0 0 0 0 0 0 0 0 • o 0 Compound of formula 61 5 1 3C, 9G, 6Y 5G, 9G 10C 10C 2C, 9G 9C 9C, 8G 10C 10C 6C, 9G 9C 9C 9C 9C IC, 9H IC, 9G IC, 9G 9G 8G 10E 5C, 9H 2C, 8G 9G 9H 2C, 9G 10E128 500 21 22 Table 2f Dose kg / ha After plant emergence Cotton bean sorghum maize soybean wheat oat deaf rice weed weed one-sided bloody morning glory marsh sand sedge Before plant emergence sorghum maize soybean wheat oat deaf rice weed unit ronna finger swallowtail bindweed cassia sedge sand 1 Compound of formula 62 1 9C 6C, 9G 1 2C, 9G 7U, 9G 4C, 9G 2C, 7G IC, 8G 3C, 9G 9C 6C 10C 10C 9C IC, 9G 4C, 9G 2C, 9G 8H I 9G 2C, 9H 2C, 9H 2C, 9H 2C, 9G 9C 9H 1 2C, 9G 10E 1 Compound of formula 63 0 ^ 5 9D, 9G, 6Y 3H, 6C, 9G 9C IC, 9G 5C, 9G 9C 9C 9C 10C 2C, 5G 10C 9C 9C 4C, 9G 3C, 9H and 2C, 9H 3C, 7H 3C IC, 9G 10E 2C, 9H IC, 3G 9G 9H 2C, 9G 10E 1 Compound of formula 64 9D, 9G, 6Y 6C, 9G 3C, 9G 3U, 9G 3C, 9G IC, 3G IC, 2G 2C, 9G 10C IC, 3G 3C, 9G 6C, 9G 3C, 7G 2C, 7G 2C, 9G IC, 9G 9H 0 IC, 5G | 9H 3C, 8H IC, 3G IC, 9H 9H 1 9G, 3C IC, 9G 1 Compound of formula 65 iM) 5 _ 4C, 6G, 6Y 3H, 6C, 9G IC, 6H IC, 5G 2C, 9G 0 ^ 0 8G 3C, 7H 1C, 3G 9C 6C, 9G 3C, 5G IC, 3G 2C, 7G IC, 8G IC, 9H 0 0 2C, 5G IC, 5H 0 2C, 9G 9H 6C, 9G 3G 1 Table 2g Dose kg / ha Po plant emergence cotton beans sorghum maize soybean wheat oats deaf rice weed weed one-sided stick bloody morning glory cornflower cassia sand sedge Before plant emergence sorghum maize soybean wheat oat deaf Iris single-sided weed bloody bindweed cassia [sand sedge | 1 Compound of formula 66 0.1 2G 3C, 3H, 7G IC, 3G 1 0 2C, 9G 0 0 0 o 0 6C, 9G 4C, 9G 2C IC, 2G 0 0 1 0 0 0 0 0 0 0 0 0 0 | 1 Compound of formula 67 1 0.05 5C, 9G, 6Y 9C 9C IC, 2G 2C, 8G 0 2G 4C, 9G 1 3C, 9H 2C, 4G 9C 10C 5C, 9G 9G 2C, 9G 2C, 5G IC, 4H, 0 IC, 6G 3C, 9H 2C, 8H IC 9G 9H 2C, 8G 9G 1 1 Compound of formula 68 1 0fi5 and 9C 9C 3U 2C 2C 0 IC 2C 10C 3C 9C 10C IC 2C, 9H 2C, 8H 2C, 5G 3G IC , 8G 2C, 8H 2C, 9H IC, 3G 9G | 9H 2C, 8H 9G | Compound of formula 69 0 ^ 05 € 4, 9G, 6Y 5C, 9G and 10C 2C, 4G IH, 6G 1 0 I 5G [7G I 3C, 7H 1 2C, 5G 1 2C, 9G 1 9C and 5G 8G 2C, 9H 2C, 7H 1 2G 1 0 1 IC, 6G 1 2C, 6G I 3C, 5G 1 IC 1 IC, 6G 1 9H | IC 5G 1128 500 23 24 Table 2h Dose kg / ha After plant emergence cotton bean sorghum maize soybean wheat oat deaf rice weedweed one-sided bloody morning glory turnip cassia sand sedge Before plant emergence sorghum maize soybean wheat oats daffodil rice weedworm one-sided bloodworm | Cassia | Sand sedge | 1 Compound of formula 70 0 ^ 5 9C 9C IC IC IH 0 2G 0 2G IC 9C 10C 2G IC, 7G IC, 3G IC 0 0 2C IC, 4H IC 9G 9H and 2C, 9H 2G | 1 Compound of formula 71 0.4 0 IC 4G 0 0 0 0 2G 0 5G 3G 3G 0 3G 0 0 IH 0 0 0 0 2G '3G 5H 0 0 | 1 Compound of formula 54 1 3G 0 0 0 7G 0 0 0 0 0 0 2G 0 0 0 IH 0 0 0 0 0 0 0 0 0 | 1 Compound i of formula 55 IH 0 1 2G 3G IH 0 0 4G 0 3G 2G IC 0 4H 0 IC, IH 0 0 2C 0 IC 0 2C 0 3G Table 2i [Dose kg / ha | After plant emergence Cotton beans sorghum maize soybeans wheat 1 deaf oats Iryz oatworm I cassia sands sedge Bloody bindweed cassia sand sedge Before plant emergence sorghum maize soybean wheat oats deaf rice one-sided weedworm cassia sand sedge 1 Compound of formula 56 0fi 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 Compound of formula 57 3C, 9G, 6Y 2C 0 2C, 3G 2H 0 0 0 0 0 2C, 6H 2C, 6G 0 0 0 0 0 0 0 0 0 0 0 0 0 1 Compound of formula 58 IC, 2G, 6Y IC 3G IC 2H 0 0 4G 0 IC IC 3C, 6H IC 0 0 0 0 0 0 0 0 o 9H 0 0 1 Compound of formula 59 M 0 0 0 0 0 0 0 0 0 0 3B 0 0 0 0 0 0 0 0 0 0 0 0 0 0 | 25 128 500 Table 2k 26 Dose kg / ha Post-emergence cotton beans sorghum maize soybean wheat oats deaf rice weed weed one-sided bloody finger morning glory marshes 1kassia, sand sedge Before emergence, it grew in sorghum maize Isoja wheat oat deaf rice one-sided weedworm bloody morning glory and turnip 1 1 cassia | sand sedge | Compound o 2 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 0 formula 74 1 6 3C 3C 0 0, IC 0 0 0 IC 0 0 0 IC 0 IC, 5G 2C, 5G 0 0 IC, 4G IC 5C, 8H 2G 3C 2C, 8H 3G 0 Compound o 2 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 0 formula 75 6 1 0 2C 2C 0 3G 0 0 0 0 0 IC, 3G 0 0 0 2C IC, 2G 0 0 a IC 5C 0 2C 5H 5G 0 Table 21 Dose kg / ha Post-emergence cotton sorghum maize soybean wheat oats deaf rice one-sided weedworm bloody morning glory cassia sand sedge sugar beet Before plant emergence sorghum maize soybean wheat oat deaf rice foulweed one-sided stick bloody bindweed turnip cassia sand sedge sugar beet Compound of formula 76 0.05 2C, 8G, 9G 3CU, 9G, 6Y 4CU, 9H 3C, 9H 2C, 9G 2C, 9G 5C, 9G 5C, 9H 6G 2C, 4G 5C, 9G 3C, 5G 2C, 9G 9C 5C, 9H 5C, 9H 4C, 7H 2C, 8G 2C, 8G 10E 2C, 3H 2C 2C, 8G 2C, 8H 3C, 9G 9C Compound of formula 77 0.04 9C 9C 10C 5U, 9C 9C 2C, 9G 3C, 9G 9C 9C 5C, 9G 9C 10C 9C 10C 4C, 9H 6C, 9G 9H 3C, 9G 3C , 9G 10E 7C, 9H 3C, 9H 2C, 9G 9H 5C, 9G 10E Tabe Dose kg / ha After plant emergence cotton beans sorghum maize soybean wheat oats deaf rice weed weed one-sided stalk bloody morning glory turnip cassia sand sedge sugar beet Before plant emergence sorghum maize soybean wheat oats wheatgrass weedworm Cassia Sand Sedge Sugar Beet | Ia 2l 1 Compound of formula 78 0.05 ic, IC 0 0 2C, 0 0 IC 0 0 2C, 2G 2G 0 2C, 0 2C, 2C, 4G IC 2C 2C 1 ° 5G 6G IC 0 7H 1H 1 7G 5G 2H 5G 2H Compound 1 of formula 1 79 1 0.05 | 1 9C 9C 9C 3U, 3G 2C, 8G 3G 3C, 9G 6C, 9G 5C, 9H 3C, 7G 10C 10C 5C, 9G 9C 9C 4C, 9H 2C, 8G 9C 2C, 8G 3C, 9G 4C, 9H 2C, 8H 1 IC, 2G 1 9C 9H 3C, 5G 10E 5C, 9G | 128 500 VU Tabel 1 Dose kg / ha 1 Post-emergence 1 beans 1 cotton 1 sorghum 1 corn 1 soybeans 1 wheat 1 oats deaf rice 1 one-sided weed 1 bloody finger 1 morning glory 1 turnip 1 cassia sand sedge 1 sugar beet Before plant emergence I sorghum 1 maize soybean I wheat oat deaf rice 1 weed weed 1 stalk bloody cornflower bindweed cassia. sand thuja sugar beet a 2m 1 Compound of formula 80 0.05. 5C, 9G, 6Y 5C, 9G 5C, 9G 4C, 9G 3C, 9G 4C, 9G 4C, 9G 5C, 9G 3C, 9H 3C, 9G 2C, 5G 5C, 9G 2C, 5G 3C, 6G 4C, 9G 5C, 9H 4C, 9H 4C, 5Q 4C, 9H 5C, 9H 10E 2C, 9H 4C, 9G 9G 9H 8G 4C, 9G 4C, 9G | Compound and formula 81 0.05 9C 5C, 9G 1 2C, 9H 1 9C 5C, 9G 0 3C, 5G 5C, 9G 4C, 7H 5G SIL 'I 10C 5C, 9G 4G 10C 4C, 9H 2C, 9G 4C, 8H 2G 0 10E 4C, 7G IC 3C, 9G 9H 5C, 9G 5G 9C I It should be noted that some compounds, such as compounds of formulas 47, 48, 53-56, 59 and 60, show either little or no activity in the subject concentration range. It is believed that they could nevertheless exhibit herbicidal activity with higher doses. Test B. 2 flask-shaped plastic vessels were filled with Falsington clay loam soil with the addition of fertilizers and lime. In one pot, maize, sorghum, waxweed and several different grass weeds were planted. The second pot was planted with cotton soybeans, sand sedges (Cyperus rotundus) and other broadleaf weeds. The following grasses and broadleaf weeds were planted: Digitaria sanauinalis, single-sided chwaistndee (Echinoohloa crusgalli (Echinoohloa crusgalli), algae oats. Avena fatua), Aleppo sorghum (Sor- gum halepense), dallisgrass (Paspalum dilatatum), Wlosnica (Saftaria faberii), iStoklosa rye (Bromus secaLfeius), mustard (Br & ssica airvensis), turnip (Xanthium penisylcaniicum) (Arna- caniicum) 15 20 so 40 45 50 60 65 ranthus retroflexus), bindweed (Ipomoea hederacea), cassia (Cassia tora), spiny safflower (Soda spinosa), safflower (Abutilon theophrasti) and woodworm (Datura stramonium). with a diameter of 12.5 cm, the prepared soil was also filled and the rite and wheat were sown there. Sugar beets were sown in another pot with a diameter of 12.5 cm. The above 4 reservoirs were treated prior to plant emergence with various test compounds falling within the scope of the invention. 28 days after treatment, the chemical effect of the treatment was analyzed and visually assessed based on the scoring system previously described for Test A. Data are summarized in Table 3. Test C. Z From the results obtained in this study, it is evident that 2 of the compounds tested have particularly high herbicidal activity. In this experiment, these compounds were applied to the soil prior to plant emergence. Plastic pots 25 cm in diameter were used, filled with Fallsington loam-loam soil. In one series of pots, weeds were sown, the seeds of which were mixed with 1.2 ohm coarse soil (homogeneous mixture). The following species were selected: Aleppo sorghum (Sorghum halepense), one-sided weed (Echinoohloa grusgalli), bloodstaff (Digitaria sanguinalis), trichinella (Setaria faberii), sorghum (Abutilon theophrasti), white weed (Batura .stramonica), arvensycais (Brassica). ) and white quinoa (Amaranthus retroflexus). In the second series of pots, the following crops were sown using 1 to 4 species in one pot: maize (sowing depth 3.7 cm), corn, soy, sunflower, Clinton's oat , wheat, Black Valentine beans, rice, sorghum, peas, flax and peanuts (all at a depth of 2.5 cm), cucumbers, cabbage, alfalfa, safflower, sugar beet, tomatoes, spinach, barley and waxweed (all at a depth of 1.2 cm). Immediately after sowing, the test compounds dissolved in a solvent that is not toxic to plants were applied to the soil surfaces. One pot of weed samples and one of each crop species were left untreated for comparison. The treated and untreated pots were immediately watered with water so that the irrigation would compensate for the rainfall of 4 mm and then stored in a greenhouse for several weeks. Visual evaluation of the weeds and crops was done 28 days after treatment, based on the evaluation system described above. above for text A. The data are given in Table 4. Test D. 2 plastic pots 25 × 4 cm in diameter, lined with polyethylene lining, were filled with Fallsington clayey loam soil. In one pot, seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), deaf oat (Avena fatua), roof pile (Bromus tectorum), rye grass (Bromus secalinus), field grasshopper (Alopecuiruis myosuroides) were sown. annual (Boa annua), saplings (Setaria viridis), common couch grass (Agropyroa repens), sycamore (Lolium multi florum) and bromus rigidus. 128 500 29 30 Table 3 Pre-emergence use Dose kg / ha bloody weed sorghum sorghum deaf oats Aleppo sorghum dallisgrass [hairwort waxweed varnish roofing pile sugar beets maize mustard turnip quinoa white sedge ^^ sand cotton bindweed cassia mallow thorn safflower daffodil wheatgrass 3 7 , 3H 9G, 9C 6G 8G, 7C 7G 6G, 3C 8G, 9C 8G, 9C 10C 5G, 3U 10C 6G 10C 10E 8G 5G 8G, 8C 6G 9G, 8C 7G, 3C 8G, 5H 8G, 3H 0 0.12 8G , 3H 9G, 9C 10C 10C 10C 9G, 9C 8G, 5C 10C 9G, 9C 10C 8G, 5H 10C - 10E 10E 9G, 5C 9G, 9C 10C 9G, 8C 10C 9G, 8C 1 9G, 8C 10E 3G Compound of formula 33 | 0.03 7G, 3H 9G, SC 10C 8G, 5C 9G, 9C 8G, 3H 5G, 3C 8G, 9C 10E 10C 7G, 5H 10C 5G 7G 6G 6G, 3H 7G 7G, 4C 6G, 3H 8G, 8C 9G, 9C 7G, 5H 8G, 7C 5G 0.12 8G, 3H 10C 10E 9G, 9C 10C 8G, 3H 10C 10C 10E 10C 10C 10C lOC 10E 10E 9G, 8C 9G, 5C 9G, 9C 9G, 6C 9G, 9C 9G, 9C 9G , 8C 10E 8G, 9C Table 3a Dose kg / ha bloody weed sorghum sorghum deaf oats Aleppo sorghum dallisgrass hairwort waxweed varnish roofing pile sugar beets maize mustard quinoa quinoa white sedge cotton bindweed wheatgrass 1 soybean moss martin 1 0 2G 2G 0 0 0 0 0 0 - 0 5G 0 0 0 0 3G 0 - 0 0 0 3G 0 Compound 0.015 0 2G 4G 0 3G 3G 3G 2G - 4G 0 7G, 3C • lOE 0 0 3G 0 0 0 0 0 6G, 36 0 formula 34 0.03 5G 8G, 3H 10C 10C 10C 6G 3C 10C 10E 10C 10C 10C 7G 9G, 9C 10E 8G, 3C 8G 9G, 8C 4G 8G, 5E 8G, 8C 8G, 5H 10E 5G 0, 12 6G 9G, 9C 10E 10C 10C 8G, 3H 7G, 3C 8G, 3C 10E 10C 10C 10C 8G, 5H 10C 10E 9G, 7C 9G, 7C 9G, 8C 10C 9G, 8C 9G, 9C 9G, 8C 10E 7G, 3C31 128 500 31 Table 3b Dose kg / ha bloody weed weed sorghum sorghum deaf oat sorghum Aleppo dallisgrass hairwort waxweed waxwort roofing sugar beet sugar beet maize mustard turnip quinoa white sedge sands cotton bindweed cassia sallow thorns soybean rice 6 , 3H 4G 4G, 3H 4G 4G 6G 6G 6G, 6C 3G 10E —— 5G, 5C 7G 4G 4G 6G. 5G, 3C 5G, 3H 3G 2G | 3G formula 67 1 0.25 4G 6G, 5H 8G, 5H 4G 6G, 3H 5G 6G, 3H 7G 7G 8G, 9C 4G 10E 8G, 7C 9G, 9C 10E 8G, 3H 8G, 9C 8G, 8C 6G, 3C 8G , 8C 5G, 5C 5G, 3H 5G 0 Relationship o 0.06 2G 4G 4G 3G 4G 3G 0 2G 0 9G, 8C 2G 8G, 8C 8G, 5H 4G 4G 8G, 3H 9G 5G, 3C 6G, 2C 7G, 3H 7G . 3C 3G 0 0 | formula 68 I 0.25 2G 5G 4G, 2H 3G 3G 0 2G 4G 3G 10C 4G 8G, 9C 10C 6G, 4C 6G 9G, 5C 9G, 3C 7G, 8C eG, 3C 8G, 9C 8G, 5C 4G 0 0 in the second the pot was sown with seeds of barley brine (Salsola kali), mustard (Descuraina pinnata), knotweed (Polygonum pensylvanicum), centipede (Sisymbrium altissium), tassel (Kochia scoparia), pasture-shepherd's purse (shepherd's shepherd's) a weed called Mafcricaria inodora, black nightshade (Solanum nigrum), common mustard (Barbarea vulgaris), field mustard (Brassica kaber) and wild buckwheat (Polygonum convolvulus). Both of these pots were treated prior to plant emergence. At the same time, two pots in which the above-mentioned plant species grew, were treated "after plant emergence". The size of the plants at the time of treatment was 1 - 15 cm, depending on the plant species. The compounds used were dissolved in a solvent non-toxic to the plants and sprayed on the top of the pots. For comparison, an untreated control and a control sample of the solvent alone were included. All test samples were stored in a greenhouse for 20 days, and the treated samples were immediately compared to the control samples. and the effects were assessed visually. The results obtained are summarized in Table 5, which shows that some of the compounds encompassed by the scope of the invention are useful for controlling weeds in cereal crops, such as wheat and barley, before and / or after emergence of the plants. Test E. The test samples were prepared and applied directly to the rice water 3 days after the rice was transplanted. Poor evaluation of the plants was made after application at fixed time intervals. The results are summarized in Table 6 below. As can be seen the compounds of the invention can be used to control selective weeds in rice. Test F. The test compounds dissolved in a non-phytoxic solvent were used for general spraying of foliage and surrounding soil of selected species. plants. One day after treatment, it was noticed that the plants were quickly damaged by burning. Approximately 14 days after treatment, all species were visually compared to the untreated control samples and the treatment results were assessed based on the scoring system previously given in text A. The results are given in Table 7. All plant species were sown in sandy loam soil. Woodston clay and grew in the Greenhouse. Plastic pots filled with soil (25 cm in diameter, 13 cm deep) grew the following types of plants: soybean, cotton, alfalfa, corn, rice, wheat, sorghum, sorghum ( Abutilon theophrasti), hemp (Sesbania exaltata), Cassia (Cassia tora), bindweed (Ipomoea heoeracea), Datura stramonium, turnip (Xanthium pensylvanicum), bloody toad (Digitaria128 500 33 84 Table 4 Dose kg / ha cotton maize soybean peanuts sunflower oats wheat sorghum sugar beet peas flax alfalfa beans spinach cabbage tomatoes rice safflower cucumber meadow grass barley broad-leaved grasses 0.0035 - - - - - - - - - - - - - - - - - - - - 3G 0 Compound 0.0075 - - - - - - - - - - - - - - - - - - - - - 4G 0 with formula 32 0.0150 _ —¦L - - - - - - - - - - - - - - - - - - - - 6G, 2H 2G 0.03 | 5G, 3C 7G, 3H 4G, 2H 6G 5G 4G 2G 7G, 5H 9G, 9C 10E 6G 8G, 6C 0 8G, 5H 8G, 6C 4G 6G 7G, 4C | 5G 7G 1 3G - - 1 Table 4a Dose kg / ha maize 1 cotton Isoja 1 peanuts 1 sunflower seeds wheat sorghum sugar beets peas »flax alfalfa beans spinach cabbage tomatoes rice safflower cucumber meadow grass broadleaf barley grasses 1 0.0075 1 - - - - - - - - - - - - - - - - - - - - 5G, 3C 6G, 3C Compound | 0.015 - - - '- - - - - - - - - -, - - - - - - - 7G, 5C 8G, 4C formula 33 0.030 - - - - - - - - - - - - - - - - -' - - - .— 9G, 8C 9G, 6C | 0.06 1 9G, 9C 10E 9G, 5H 1 8G, 3H I 9G, 5H 6G, 2C 5G I 10E 10E 10E 10E 8G, 6C 8G, 5H I 9G, 9C I 6G, 7C I 5C, SG 1 10E 1 8G . 7C AND 9G, 5H AND 6G, 5H | 8G, 7C - I - I128 500 35 36 Table 5 Pre-emergence of plants I Dose kg / ha 1 Barley wheat sheep deaf roofing pileus rye grass field grassland annual grasshopper 1 green hair Iperz righteous polypsophyllum named Matricaria inodora black nightshade common mustard wild buckwheat I 0.002 0 0 0 3G 5G 3G 5G 0 3G 0 2G 0 6G - 3C, 8G IC 3C, 5G 4G 2C, 4G 2C, 7G 5C, 6G 3G Compound 0.008 0 0 0 2C, 5G 4C, 7G 5C, 6G 2C, 6G 2G 3C, 5G 3C, 5G 2C, 4G 0 8C, 8G - 10C 5G 8C, 8G 7C, 8G 4C, 6G 4C, 8G 8C, 8G 2C, 4G with formula 32 0.008 0 0 0 IG 3G 2G IC, 2G 3C, 4G 0 0 0 IG 8C, 8G - 7C, 7G 3G 9C, 8G 7C, 7G 6C, 7G 7C, 7G 7C, 7G IC, 2G 0.015 0 IC, 6G 3C , 7G 5C, 7G 10C 10C 7C, 8G 3C, 5G 8G 4G 2C, 5G 8C, 7G 10C - 10C 9C, 8G 10C 10C 8G 10C 10C 3C, 6G Table 5a Dose kg / ha Post-emergence barley wheat sheep deaf roof Rye leaflet fowl field panicle one annual green hair couch grass common wheatgrass stoklosa stoklosa [brine spiny mustard Irdest spicy stulisz lofty mellow tasznik weed Matricaria inodora black nightshade mustard common mustard wild buckwheat 0.002 0 0 0 3G 4G 2GC 7G 6G 2 3GC 7G 6G 10C - 4C, 6G 3G 10C 7C, 7G 4G 3G 10C 2C, 4G Compound 1 0.008 0 0 IC 5C, 7G 1 8C, 7G [4C, 5G 3C, 6G 7C, 7G 6G 2G 1 5G 10C 10C - 10C 4G 10C 10C 4C, 6G 10C 10C 5C, 5G formula 32 1 0.008 0 0 0 4C, 5G 8C, 7G 7C, 7G 3C, 5G 7C, 7G 2C, 3G 0 0 9C, 7G 10C - 10C 10C 10C 9C, 7G IC, IG 10C 10C 6C, 5G 1 0.015 0 3C, 5G 3C, 2G 3G 10C 10C 5C, 4G 3C, 4G 6C, 5G 3G 2G 1 10C 1 10C - I 10C 8C, 7G 10C 10C 0 10C 10C 10C128 500 37 38 Table 5b 1 Dose kg / ha wheat 1 lamb deaf roof rye stock [field foxtail] annual pea 1 green hair couch grass common ryegrass (stiff brine spiny brine] mustard jrdest spicy stew and j weed Matricaria inodora black nightshade common mustard Field mustard 1 wild buckwheat Compound Pre-emergence 0.03 0 1C, IG 0 2C, 7G 5C, 8G 3C, 7G 5C, 7G 7C, 7G 2C, 3G 1C, 3G 0 2C, 3G 10C - 10C 7C, 8G 10C 7C, 8G 7C, 7G 8C, 9G 8C, 8G 3C, 4G 0.06 2C, 3G 6C, 8G 8C, 8G 10C 10C 10C 10C 9C, 8G 10C 4C, 7G 5C, 7G 8C, 8G 10C - 10C 10C 10C 10C 3C, 8G 10C 10C 4C, 8G of formula 32 Post-rise 0.03 0 2C, 2G 2G 7C, 7G 10C 10C 6C, 7G 7C, 8G 3C, 6G 2C, 4G 2C, 3G 10C 10C - 10C 10C 10C 9C, 8G 3C, 7G 10C 10C '7C, 6G 0.06 | 1C, 2G 7C, 6G 3C, 3G 3C, 4G 10C 10C 10C 7C, 6G 7C, 6G 4C, 5G 3C, 5G 10C 10C - 10C 10C 10C 10C 4C, 5G 10C 10C 10C Table 5c I Dose kg / ha and 1 Before the rise of plants;] wheat 1 barley 1 deaf oats 1 roof and rye stokloss I field grass j Annual pea green trichinella Iperz peculiar 1 multiflower trichomes 1st stiff spiny brine | mustard Jrdest spicy bitter brine 1 Black mustard mustard Field mustard 1 wild buckwheat 0.002 0 0 0 6G 5C, 7G 1 3C, 6G 1C, 6G 0 4G 3G 5G 0 3C, 8G - 7C, 8G 2G 8C, 8G 5C, 8G 3C, 4G I 8G 7C, 8G 2C, IG Compound 0.008 0 3G 2C, 5G 7C, 7G 10C 7C, 7G 7C, 7G 4C, 5G 3C, 6G 5C, 7G 6G 1C, IG 8C, 9G - 10C 5G 8C, 8G 7C, 8G 3C, 4G 2C, 9G 8C , 8G 3C, 4G formula 33 0.008 0 <3C, 4G 2G ¦ 3C, 7G 5C, 8G 3C, 7G 2C, 5G 2C, 4G 4G 5C, 7G 3C, 4G 3C, 4G 7C, 8G - 10C 7C, 8G 10C 7C, 7G 5C, 6G 7C, 7G 7C, 8G 3C, 2G 0.015 »C, 2G 5C, 7G 8C, 8G 10C 1 10C 10C 10G 1 6C, TG 8C, 9G 9C, 9G 9C, 9G 9C, 9G 10C - 10C 8C, 9G 10C and 2C, 7G 10C 10C 3C, 4G • 128 500 39 40 Table 5d Dose kg / ha After emergence wheat barley oats deaf stokle roof rye grass field grassland field plant annual green hair grasshopper common wheatgrass stoklosa stiff brine spiny mustard knotweed spicy knotweed lofty sandstone tasznik weed Matricaria inodora black nightshade mustard common field mustard | wild buckwheat 0.002 0 0 0 3C, 5G 6C, 7G 2C, 6G 5C, 6G 3C, 5G IC, 6G IC, 5G 4G 5C, 4G 10C - 7C, 8G 5G 10C 10C 2G 10C 10C 2C, 2G Compound 0.008 IG 3G 2C , 5G 7C, 7G 10C 7C, 7G 10C 4C, 5G 4C, 6G 3C, 6G IC, 7G 8C, 7G 10C - 8C, 8G 10C 10C 10C 3C, 5G 10C lOC 3C, 5G Formula 33 0.008 IG 2C, 3G 5G 7C, 7G 10C 7C, 7G 6C, 5G 7C, 8G 6G 3C, 6G 3G 10C 10C - 10C, 10C 10C 7C, 7G IC, IG 8C, 8G 10C 6C, 6G E 0.015 1 5C, 5G j 7C, 6G j 7C , 7G I 7C, 7G 10C 10C 1 10C | 6C, 6G V 7C, 6G 10C [; 4C, 6G 10C 10C h - | 10C \ 7C, 6G | 10C [i 10C 0 10C 10C ioc 1 Table 5e Dose kg / ha barley wheat oat deaf stoklos roofing stokloss rye foxtail grassland annual grasshopper green grasshopper scabiosa multiflorous stoklos stiff brine spiny mustard weed knotweed mackerel black mustard common mustard field 1 wild buckwheat Compound Before emergence. 0.03 2C, 4G 6C, 7G 7C, 6G 7C, 8G 10C 8C, 7G 5C, 6G 4C, 6G 7C, 7G 7C, 8G 6C, 7G 5C, 6G 9C, 9G - 10C 9C, 8G 10C 7C, 8G 7C , 6G 10C 9C, 8G 1 4C, 5G 0.06 4C, 6G 8C, 8G 9C, 8G 10C 10C 10C 10C 9C, 9G 9C, 9G 10C 9C, 9G 10C 10C - 10C 9C, 9G 10C 10C 5C, 8G 10C 10C 5C, 6G of formula 33 Post-emergence [0.03 IC, 2G 4C, 6G 5C, 6G 8C, 7G 10C 10C 10C 8C, 8G 4C, 6G 5C, 7G 4C, 4G 10C 10C - 10C IOC IOC 8C, 7G 3C, 4G 10C 10C 7C, 8G 0.06 [7C, 7G [10C l 8C, 7G I 10C 10C [10C l 10C [7C, 7G f 10C f 10C L 9C, 8G f 10C and 10C l 1 10C IOC ioc I li IOC 2G | 10C [10C f 10C | 128500 41 to Table 5f Dose kg / ha wheat 1 barley 1 deaf oat J roofing leaf 1 rye leaf] Field fowl Annual loach Green exfoliating lperz true 1 polymorphism and stiff leaflet I common spiny brine jmietelnik Itasznik ychwast named 1 Matricaria inodora Ipsianka black 1 common mustard I field mustard (wild buckwheat | Compound Pre-emergence 0.008 | 0.43 0 2G IG 4G 2C, 5G 7C, 7G 3C, 4G 2C, 3G 0 3G 0 0 4C, 5G - 7G 6G 7C, 7G 6C, 7G 3C, 4G | 7G 5C, 7G 0 | IC, 2G 7C, 6G 7C, 7G 10C 10C 10C 5C, 6G 5C, 4G 3C, 4G 7C, 7G 10C 7C, 7G 9C, 9G - 10C 10C 10C 7C, 7G 5C, 6G 7C, 7G _ 1 7C, 8G 2C, 3G: with formula 33 Post-rise 0.008 0 0 0 6C, 7G 7C, 7G 4C, 5G 4C, 6G 2C, 4G 2C, 3G 3C , 6G IC, 2G 3C, ZG 8C, 7G - 10C 4G 9C, 8G 6C, 5G 4G 2C, 5G 10C 2C, 2G 1 9'e3 | IC, 2G 4C, 6G 7C, 5G 7C, 7G 10C 10C 5C, 7G 6C, 7G 4C, 6G 5C, 6G 3C, 4G 10C 10C - 1 10C 10C 10C 9C, 8G 8C, 8G 10C 10C - 5C, 6G 1 Table 5g [D bench kg / ha | wheat 1 barley and deaf oats 1st moss roof rye lartoclass rye grasshopper grassland annual pea green trichinella couch grass 1 wheatgrass stiff brine barbed brine mustard lrdest spicy grasshopper 1 Ipsichnik polypolite weeds Pre-emergence 1 0.015 0 0 0 3G 7G 6G 6G 2G 0 IG 2G 0 2G - 5G 0 7G 3C, 8G 4G 3C, 8G 7C, 8G 3G | | 0.06 0 0 0 6G 10C 3C, 7G 7C, 7G 3C, 5G 2G 3G 2C, 7G IG 2C, 5G - 3C, 7G 5C, 6G 3C, 8G 7C, 8G IC, 5G 10C 1 10C IC, 4G by formula 6 * 7 Post-emergence I | 0.015 0 0 0 0 1 IG 2G 2G IG 0 0 0 0 5C, 4G - 10C 0 7C, 8G 7C, 7G 2G. 7C, 7G 10C IC, 2G 1 1 ° »06 1 0 0 0 3G 3C, 5G 5C, 4G [3G 2G 0 0 2G 2G 7C, 8G - 1 10C l 0 10C 9C, 8G 4C, 5G 10C 10C 5C, 4d 143 128 500 Table 6 44 Compound of formula 32 Dose g / ha 1 4 8 reams 4 days 0 0 0 Dose g / ha 25 100, reams 1 week 0 0 and reams 4 weeks 0 0 0 Unilateral weed (Echinochloa spp.) 8 weeks 0 0 0 Eleocharis spp. I 4 weeks l 7G 8G 9G l Compound of formula 67 reams 8 weeks 0 0 Unilateral Barnyardgrass weeds 8 weeks 0 0 Eleocharis spp. 8 weeks 10C 10C Water dart 1 (Sagittaria) 8 weeks I; 0 [0 f spp), sand sedge (Cyperus rotundus), one-sided weed (Echinochloa crusgalli), trichinella (Setaria faberii), deaf oats. The following plant species: sunflower, sugar beet, mustard (Brassica arvensis). All plants were sprayed about 14 days after sowing. Some of the test compounds in this treatment are useful for post-emergence weed control in wheat. The compound of formula 70 is suitable for post-emergence weed control in soybean cultivation. Test G. This test illustrates the weed killing properties of the compound of formula 70 in relation to for broadleaf plants. 12 soybean seedlings grew oikolo in a 25 cm diameter plastic pot. The following broadleaf plant species grew in the second pot of the same dimensions: sugar beet, snails (Abutilon theophrasti), hemp (Sesbania), cassia (Cassia), mustard (Brassica arvensis), bindweed (Ipomoea hederacea), Alfalfa, Datura stramonium (Datura stramonium) and turnip (Xanthium pensyl-vanicum). Plant foliage and the surrounding soil were sprayed with the test compound dissolved in a non-toxic solvent, in the form of a spray stream at the rate of 0.015 kg / ha and then when the plant She was 17 days old. 22 days after treatment, a visual evaluation of the herbicidal effects was made based on the rating system given in Test A. The results are shown in Table 8. The above data indicate that the test compound is excellent at controlling broadleaf weeds in crops. The invention is illustrated by the following examples, in which the temperature is given in degrees Celsius, 128 500 45 46 Table 7 Sprinkling of plants and soil from above Dose kg / ha soybean Izaslaz hemp cassia cotton bindweed alfalfa bleached turnip maize bloody rice sand sedge weed one-sided weed wheat 1 large hair oat deaf sorghum mustard sunflower sugar beet 0.06 10G, 7C 10G, 7C 9C 10G, 7C 10G, 7C 9G, 5C 10G, 5C 10C 8G, 4C 8G, 3C 10C 10C 0 10G, 3C 6G 10C __ ~ Compound 0.015 10G, 7C 8G, 3C 9C 8G, 2C 7G, 3C, 9G, 4C 5C 7G, 3C 9G, 3C 9G, 7C 2C 3G, IC 10C 10C 0 7G, 3C 3G 9C "" formula 32 0.007 9G, 5C 9G, 9C 10C 9G, 5C 10G, 9C 10G, 8C 6G, 2C 0 7G 8G, 2H 5G 8G, 5C 5G 9G, 4C 0 5G 3G 8G , 3C 10C 10C 10C 0.003 9G, 5C 10G, 9C 10C 10G, 5C 10C 10G, 8C 6G, 2C 0 5G 9G, IH 0 7G, 2C 3G 9G, 2C IG 5G 3G 7G, 4U 10C 10C 9G, 9C Table 7a Dose kg / ha soybean soybean hemp cassia cotton bindweed alfalfa whitewash leathery turnip maize bloody rice sand sedge one-sided weed wheat trichomoniasis deaf oats sorghum mustard sunflower | sugar beet Compound of formula 33 1 0.06 9C 10G, 4C 10C 10G, 7C 10G, 6C 10C 10C 10C 10G, 8C 10C 10C 10C 10C 10C 9C 10C 10C 10C - - - 0.015 | 10G, 8C 5G 9C 7G, 3C 7G, 3C 8G, 2C 7C - 10G, 7C 10G, 7U 6G, IC 6G, 3C 2C 6G, 3C IC - 5C, 3C 8G, 5C - - - 1128 500 47 48 Table 7b Dose kg / ha soybean soybean hemp cassia cotton morning glory alfalfa 1 bleached leeward turnip 1 corn] bloody rice sand sedge 1 one-sided weedweed wheat large hair oat deaf sorghum mustard {sunflower 1 sugar beet 0.06 10G, 6C 7G, 2C 7C 10G, 6C 7G, 2C 9G, 4C 9C 9G, 3C 10G, 7C 10C 7G, 4C 8G, 5C 9G, 4C 10C and 8C - 10C 10C - - - Compound 0.015 10G, 4C 5G 9C 5G, 3C 10G, 6C 9G, 3C 8C - 10G, 7C 9G, 6C 0 7G, 3C 9G, 3C 9C IC - 7G, 3C 9C - - - | formula 34 1 0.007 9G, 7C 8G, 8C 8G, 5C 10G, 5C 10C 10G, 8C 7G - 4G, 5C 9G 5G, IC 9G, 7C 7G 9G, 4C 6G 0 5G 7G, 3U 10C 10C 10C | 0.003 | 10G, 5C 7G 9G, 8C 1 8G, 4C I 8G, 2C [7G, 1H 6G, 2C I 0 [3G 9G, 1H 0 9G, 7C \ 5G 9G, 2C 3G 1 0 I 4G I 9G, 6U 9G, 9C 1 10G, 9C and 9G, 9C | Table 7c Dose kg / ha soybean 1 coppice cassia cotton bindweed alfalfa bleached white turnip corn stalk of bloody rice | sand sedge weed one-sided wheat trichinella large oat deaf sorghum mustard sunflower sugar beet Compound of formula 67 1 0.12 10C 10C 10C 10C 90, 10C 9G 0 10C 2G, 5G 5G 7G, 9G, 2G 3G, 3G 7G, 10C 10C 9G, 9C IC 5C 5C 2C 3C 3C 0.06 9G, 9C 10C 10C 9G, 3C 8G, 8C 10C 5G, 3C 0 10C IG, 2C 0 4G 7G, 5C 8G, 5C 0 2C 0 5G, 2C 10C 10C 9G, 5C 0 , C15 | 9G, 7C 8G, 7C 10C 8G, 3C 4G, 4C 8G, 4C 7G 0 10C IG, IC 0 2G 0 6G, 2C 0 0 0 2G, 2C 10C 10C 8G19 12 * 500 Table 7d 1 Dose kg / ha 1 soybean f sirloin 1 hemp and cassia 1 cotton | morning glory] alfalfa bielun] Dziedzierzawa | turnip] maize f bloody stick j rice 1 sand sedge |. Weed I one-sided 1 wheat trichinella deaf oat] sorghum l mustard 1 sunflower seeds 1 sugar beet Compound of formula 70 and M2 l '• M.l 1QG, 9G, 10C! 9G, 9G, 9G, 9G, 0 10G, 0 o 0 IG 0 0 0 0 0 10C 10C 10G, 7C 7C 7C 7C 8C 8C 7C 5C Q, 0Q6 9G, aa, I 9G,! 5G 9G, 9G, 10C - 10G, 0 - 0 0 '° 1 0 0 aro 0 10C 1 ioc 10C 9C 5C 4C 5C 6C 5C 5C 0.03' 4G 10G, 5C 10G, 7C 8G, 5C 9G, 5C 9G, 4C 9G, 5C - 10G, 5C 3G, 2C 0 4G 3G 3G 0 2G 2G 5G 10G, 5C 10G, 8C and 9G, 3C 0.015 and 0 8G, 4C 8G, 6C 5G, 5C 8G, 4C 9G, 5C 5G, 2C - 9G, 5C 0 0 IG 0 0 0 0 0 0 10G, 5C 10G, 8C 10G, 5C 0.015 0 f 8G, 3C 9G, 4C 8G, 4C 8G, 4C 1 9G, 4C 9G, 5C 8G 10G, 5C IG, 2C 0 3G 0 0 0 2G IG 4G 10G, 5C 10G, 8C 9G, 3C JQ, ai5 3G 8G, 3C 5G, 4C 4G, 6C 8G, 4C 10G, 3C 7G 2C 10G, 4C 0 0 0 0 0 0 0 2G 5G 9G .IOC 9G 1 0.007 0 7G, 3C 7G, 4C 5G, 3C 6G, 3C 9G, 6C 7G, 3C - 9G, 4C 2G 0 2G 5G 2G 0 IG 0 3G 10G, 5C 10G, 80 10G, 4C Table 8 Dose soybean sugar beet (Abutilon theoph.) Hemp (Sesbania) cassia (Cassia) mustard (Brassica arvensis) morning glory (Ipomoea heder.) | alfalfa 1 Datura stramonium (Datura stramonium) turnip (Xanthium pensylv.) 0.015 0 9G 9G, 9C 8G, 8C 7G, 4C IOC 9G, 9C 8G, 4C | 0 10P, 2C ¦a. Parts and percentages are by weight unless otherwise stated. Example I. 24-hydroxyibenzenesulfonyl isocyanate methylsulfonate. 4.0 g (0.4 mol) of 2-hydroxybenzenesulfonamide methylsulfonate, suspended in 75 ml of dry xylene, is added to 4.0 (0.4 mole) of N-bitityl isocyanate and a catalytic amount of about -0.5 g of 1,4-diazobicyclo (3.2.2) octane. This mixture is rapidly heated to reflux temperature - about 135 ° C, and 4.0 ml of phosgene is slowly added at such a rate as to maintain the reaction temperature above 128 ° C. The addition of the phosgene takes about 1.5 hours. The reaction mixture is cooled to room temperature, filtered under nitrogen atmosphere and the solvent is evaporated off under reduced pressure. The infrared spectrum of the oil obtained is identical to that of 2-hydroxybenzenesulfonyl isocyanate methylsulfonate (2210 cm -1). N- / / 4,6-dimethoxypyrimidinyl-2- (aminocarbonyl) -2-hydroxybenzenesulfonamide methylsulfonate. To a suspension of 6 g of 2-amino-4,6-dimethoxypyrimidine in 10 ml of dry methylene chloride, add 1, 1 g of 2-hydroxybenzenesulfonyl isocyanate methylsulfonate. The reaction is exothermic, temperature 21-29 ° C. The mixture is stirred for 0.5 hours. The solvent is evaporated off under reduced pressure. The mixture obtained is triturated with diethyl ether and filtered to obtain 1.2 g of a brown solid, mp 165-166 ° C. There are absorption bands at 1740, 1615, 1590 and 1360 cm-1 in the infrared spectrum. Elemental analysis: Calculated: C -38.9 H -3.73, N -12.9 Found: C -38.3, H -3.63, N -13.0. Example III. 2-Hydroxy-N- (4-methoxy-6-methylpyrimidinyl) -2-aminocarbonyl) benzenesulfonamide methylsulfonate. To suspend 6 g of 2-amino-4-methoxy-6-methyl-pyrimidine in 10 ml of dry methylene chloride, 1.1 g of 2-hydroxybenzenesulfonyl isocyanate methylsulfonate are added. The reaction is mildly exothermic. The reaction mixture is stirred for 0.5 hours. The solvent is evaporated off under reduced pressure. The mixture obtained is triturated with diethyl ether and filtered to obtain 96 g of a white solid, mp 189-190 ° C. Spectrum; in infrared it shows absorption bands at 1700, 1615, 1560, 1370 cm -1. Elemental analysis: Calculated: C — 40.4 H — 3.87 N — 13.4 I Found: C —40.2 H — 3.77, N —13.6. Example IV. N- (4,6-di-1-methoxy-1,3'-tria-2ynyl) -2-ammocarlonyl) 2-hydroxybenzenesulfonamide methylsulfonate. 6 g of 2-amino-4,6-dimethoxy-1,3, 5-triazines in 10 ml of dry methylene chloride 1.1 g of 2-hydroxybenzenesulfonyl isocyanate methylsulfonate are added to the table. The reaction is mildly exothermic. The reaction mixture is then stirred for about 1 hour. The solvent was evaporated under reduced pressure. The resulting mixture was triturated with diethyl ether and filtered to give 1.4 g of a brown solid, mp 163-166 ° C. The infrared spectrum shows absorption bands at 1715. 1600, 1550 and 1390 cm-1. Following the procedure of Examples I-IV, the compounds of formula 7 listed in Table 10 are obtained. 10 Meaning of substituents in formula 7 Ri and CH, CH, CH, CH, CH, CH8 phenyl group CH , CH, CH, CH, CH2CH, CH, CH8 CH8 CH8 CH8 CH, CH8 CHtCH, CH, CH, CH, CH, CH8. CH, (CH,) ^ H, (CHJjCHt (CH,), CH, (CH I) 8CH, (CH2H, (CHt) and CH8 (CH2), CH, (CHJjCH, CFt CH8 CH8 CH2, R, 1 2 HHHHHHH 1 H 5-C1 HHHH 3-C1 3-C1 3-C1 3- C1 HHHHHH 5-C1 HHHHHHHHHHHHHH 5-C1 1 R3 1 ^ HHHHH 1 HHHHHHHHHH 5-CI 5-CI HHHHHHHHHHHHHHHHHHHHHH H 1 R * 1 * H 1 HHHHHHHH CHH8 HHH oH 1H oH oH oH oH oH oH oH oH oH NCH8 NCH3 NCH3 o O O O O o o o o o o o o o o o o o | Y 6 OCH, OCH, CH, OCH, OCH, CH, OCH, OCH, OCH3 OCH3 OCH, Cl Cl OCH3 OCH3 OCH3 OCH3 OCH3 CH, OCH, OCH, OCH, CH, CH, OCH, CH, OCH, OCH, H OH, OCH, CH, OCH, OCH, HOH, Cl OCH, OCH, | X 7 OCH, CH, r CH, OCH, CH, CH, OCH, CH, OCH, OCH, OCH, OCH, OCH, OCH, OCH, CH, OCH, CH, CH, CH, OCH, OCH, CH, OCH , CN (CH,) 2 CH, 1 OCH, CH, CH, OCH, CH, CH, OCH, CH, CH, OCH, NHCH, NHCH, CH, | Z 8 CH CH CH N N N N CN CH CH N CH CH CH CH N N N CH CH N CH CH CH H = CH CH, ¦ CH CH N N CCI CH CH CH CH N N CCI CH CH CH CH CH | Melting point [(° Q 9L 165—166 189—190 204—205 [163—166 [170—173 181—184 f 158—162 t 216—219 174: —176 1 91—96 | 228—230 [ 183—186 l 181—183 I 134 ^ 142 [165—170 1,120 (decomposition) [200 (decomposition). 220—222 l, 216-218 1 218-222 (decomposition) I 189—191 | 160—162 1 196—198 140—145 | 200—202; 201—202 150—153 1 161—163 135—140 | 172—174 [183—186 P 182—184 I 151—154 144 ^ 147 L 186—190 I 129— 131 l 224 ^ -225 f 177—179 t 179—181 l128 500 53 54 1 1 CH, CH, CH, CH, CH, CH, | CH, CH, CH, CH, phenyl group phenyl group phenyl group phenyl group phenyl 1 phenyl group J CF, CF, CF, 1 CF, CF, CF, CF, CF, CF, 2 5-Cl 5-Cl 5-Cl 5-Cl 5-CH, 5-CH, 5-CH, 5 -CH, 5-CH, 5-CH, HHHHHHHHHHH 1 HHHH a HHHHHHHHHHHHHHHHHHHHH HHHH 4 HHHHHHHHHH CH, HHHHH CH, HHH CH3 HHHHH 5 0 o O o O 0 o OOO NF 1 CH3 NF3 CH3 NF3 r CH3 6 CH, OCH, OCH, H OCH, OCH, CH, OCH3 OCH3 OCH3 OCH3 CH, OCH3 OCH, H OCH3 OCH3 CH, CH, OCH, OCH3 OC H, CH, OCH3 CH, 7 CH, OCH, CH, CH, OCH, CH, CH, CH, OCH, OCH, OCH, CH3 CH8 OCH, CH, OCH, CH, CH, CH, OCH, OCH, CH, CH3 CH3 CH, 8 CH NN CCI CH CH CH NNN CH CH NN CCI NH CH NN CH CH CH NN 9 1 204—205 180—186 184—187 210—211 171—174 181—188 180—183 159—161 178 —181 | 133—136 221—223 182—186 184—186 169—172 193—195 143—145 135—140 (decomposition) 190—193 (decomposition) 200 (decomposition) 144—148 (decomposition) 195—197 199-200 221 —224 180—182 200—201 Table 10a Meaning of substituents in formula 7 Ri CH, CH, CH, CH, R * HHHH R3 x xxx R4 HHHHQO, 0 NI CH3 NI CH3 X OCH, OCH, OCH, CH3 Y CH2CH, OCH2CF3 OCH, CH3 ZNNNN Melting point 1 (° C) 127-130 152-154 224 227 212-213 Example 5 Wettable powder. N - ((4,6-dimethoxypyrimidinyl) -2-aminocarbonyl) -2-hydroxybenzenesulfonamide alkylcaaphthalenesulfonate sodium lignin sulfonate sodium lignin sulfonate sodium sodium kaolinite. ¬ All solid particles below 5 microns 1 re-mix. - 80% - 2% - 2% - 2% - 13% 10 Example VI. Wettable powder. 2-hydro methylsulfonate: oixy-N - ((4-non-Xy-6-methylprimidinyl) -2-aminocarbonyl) benzenesulfonamide - 50% sodium alkyl naphthalene sulfonate - 2% low viscosity methylcellulose - 2% diatomaceous earth - 46% It is roughly ground in a hammer mill and then ground in an air mill so that the resulting particles are generally less than 10 microns in diameter. The product is mixed again before packaging. 128 500 55 56 Example VII. Granules. Moisten the powder, for example, for example VI - 5% attapulgite granules with a grain size of 0.84-0.42 - 95%. The pulp of a wettable powder containing 25% solids is sprinkled on the surface of the attapulgite granule in a double-bed mixer. The granules are dried and packed. Example VIII. Extruded lozenges. 2-hydroxy-N - <(4-methoxy-6-methyl-1,3f, 5-tnasinyl) -Z-ainiirKcarbide methyl sulfonate - 25% anhydrous sodium sulfate -10% calcium lignin sulfonate technical - 5% sodium alkyl naphthalenesulfonate - i% calcium-magnesium lientonite - 59% The ingredients are mixed, ground in a hammer mill and then moistened with approx. 12% of water. The mixture is extruded into a cylindrical form with a diameter of about 3 mm and the hasteim is crushed to obtain sticks with a length of about 3 mm. These pastilles can be used immediately after drying, or the dried tablets can be ground down to a grain diameter of 0 , 85 mm. Granules with a grain diameter of 0.42 mm can be packaged and handed over to use, and the finer ones are recycled into production. Example IX. Oil suspensions. N - / [(4.6-Vumethylpyrimidinyl) -2-triinoicarbonyl) -2-hydroxybenzenesulfonamide methylsulfonate - 25% polyoxyethylene sorbitan hexanoleate - 5% more high content of aliphatic hydrocarbons - 70% All ingredients are mixed and mixed in a sand mill until the particles are continuously reduced below 5 microns. The resulting thick suspension can be used directly, but is more preferably used after diluting in oil or making an emulsion in water. Example X. Wettable powder. N- /; (4,6-dimethoxy-yl, 3,5-triazinyl) -2-amino-carbonyl) -2-hydroxybenzenesulfonamide methylsulfonate - 20% sodium alkylnaphthalenesulfonate - 4% lignin sulfonate - 4% low viscosity methylcellulose - 3 % attapulgite - 69% The ingredients are mixed carefully. After grinding in a hammer mill, particles substantially less than 100 microns are obtained, the material is remixed and sieved to separate particles greater than 0.3 mm in diameter and packed. Example XI. Granules with a low concentration of the active ingredient. N- / f (4,6-dimethylformamide 4,6-d-dimethylformamide) methylsulfonate -2- (methyl) -aminocarbonyl) -2-hydroxybenzenesulfonamide - 1% N, dimethylformamide - 9% attapulgite granules with grain size 0.84-0.42 min. - 90% The active ingredient is dissolved in the solvent and the dust-free granules are sprayed with this solution in a double-trough mixer. After spraying with the solution is finished, the mixture is stirred for a short time in a mixer and the finished granules are packed. Example 12 Aqueous suspension. N-, B-dimethyl-l, jS-triazinyl] -amino-carbonyl) -2-n-hydroxybenzenesulfonaphinide methylsulfonate - 0.3% * oliethyl glycol dodecyl phenol ether - 0.5% disodium phosphate - 1% 5 phosphate monosodium - 0.5% polyvinyl alcohol - 1% water - 50.7% The ingredients are mixed and ground together in a sand mill to give particles substantially less than 5 microns. Example XIII. Solution. N- (4.6-vymethylpyridinyl) -aminocarbonyl) -2-hydroxybenzenesulfonamide methylsulfonate sodium salt - £% 15 water - 95% The salt is added directly to the water while stirring and the resulting solution can be packaged for use. 20 Example XIV. Granules with a low content of active ingredient. 2-Hydroxy- (N-4H-methoxy-6-methylpipymdidinyl) -a-aminocarbonylHbenzenesilfamide methylsulfonate - 0.1% attapulgite granules, size 25 0.84-0.42mm - 99.9% The active ingredient dissolves in the solvent and this solution is sprayed on the dust-free granules in a double-trough mixer. After spraying is complete, the material is heated to loosen the solvent, then allowed to cool and then packaged. Example XV. Granules. N- / (4,6-dimethoxypyrimMynyl) -2-aminocarbonyl) -2-hydroxybenzenesulfonamide methylsulfonate - 80% 35 wetting agent - 1% technical ligninunhonate salt (containing 6-20% natural sugars) - 10% attapulgite clay - 9 % The ingredients are mixed and ground as far as hand - 49 measurements less than 149 microns; The material is then introduced into the fluidization granulator and the air stream is regulated so that the material is gently fluidized and the fluidized material is sprayed with finely divided water droplets. Fluidization and spraying are continued until a; granules with the desired dimensions. Spraying is discontinued while fluidization is continued, preferably by heating, until the water content is reduced to the desired level, typically less than 1%. Then the material is discharged, sifted to the desired dimensions, usually 1410-1490 microns and packed. Example XVI. Concentrates with a high concentration of the active ingredient. Methylsulfonate NV (4,6-dviumetQxy-1,3,5-triazinyl) -2-aminocarbonyl) -2-hydroxybenzenesulfonamide - 99% aerosol silica - 0.5% amorphous synthetic silica - 0.5% 60 Ingredients mixes it is ground and ground in a hammer mill to obtain a material substantially all of which has a particle size of less than 03 mm. The concentrate can then be processed if necessary. g5 Example XVII. Wettable powder. Methyl-128 500 57 58 sulfonate 2-hydroxy-N - / (4p4-methoxy-6-methyl-1,3,5-triazinyl) -2-aixiinocarboyl) -benzenesulfuramide - 90% dioctyl sodium sulfosuccinate - 0.1% fine grain synthetic silica - 9.9%. The ingredients are mixed and ground in a hammer mill to obtain particles generally less than 100 microns in size. The material is sifted through a suitable sieve and then packed. Example XVIII. Wettable powder. N - / (4,6-dimethyl-1,3,5-triazinyl) -2-anionocarbonyl) -2-hydroxybenzenesulfonamide methylsulfonate - 40% sodium lignimosulfanate - 20% bentonite clay - 40% The ingredients are mixed thoroughly, first it coarsely grinds in a hammer mill and then in an air mill, so as to obtain particles, especially with dimensions below 10 microns. The material is mixed again and then packed. Example XIX. Oil suspension. 2-hydroxyHN - ^ (4-methoxy-6-methyl-1, 3,5-triazinyl) -2-aminocarbonyl) benzenesulfonamide 1-propylsulfonate - 35% mixture of polyalcohols and carboxylic acid esters and sulfonation products formed by refined petroleum, oil soluble - 6% xylene - 59%. The ingredients are combined and ground together in a sand mill to obtain particles with a grain size of less than 5 microns. The product can be applied directly, spread in oil or emulsified in water. Example XX.- Powder. N - / (4.6 ^ Vumethoxypyr3niiidinyl) -2-aminocarbonyl) -2-hyidroxybenzenesulfonaniide 1-propylsulfonate - 10% attapulgite - 10% pyrophyllite - 10% The active ingredient is mixed with attapulgite and then passed through a hammer mill so that to obtain particles substantially less than 200 microns. The base concentrate is then mixed with powdered pyrophyllite to obtain a homogeneous mixture. Claims 1. A herbicide containing an active substance, a carrier or a solid or liquid diluent and optionally auxiliary substances, such as surfactants, characterized by the fact that the active ingredient contains a compound of formula 7, in which Q is oxygen or NR5, Rx is an alkyl group of 1-4 carbon atoms, trifluoromethyl or phenyl, R2 is hydrogen or chlorine, or methyl, R3 represents a hydrogen or chlorine atom, R4 represents a hydrogen atom or a methyl group, and R5 represents a methyl group. X represents a group of the formula N (CH3) 2, NHCH3, an alkyl group of 1-2 carbon atoms, a methoxy group, an alkenyloxy group of the formula OCH2CH = CH2 or a group of the formula OCH2CF3, Y is a hydrogen or chlorine group, methyl or methoxy group and Z is a methino group, CH, nitrogen atom or a group of formula CCl, where when Y is chlorine, Z is not nitrogen and X is NHCHS or the methoxy group when Y is a hydrogen atom then X is a methyl group and Z is not a nitrogen atom. 2. The measure according to claim A compound according to claim 1, characterized in that the active ingredient is a compound of the formula 7, in which Rj is an alkyl group of 1-3 carbon atoms or a trifluoromethyl group, Q is an oxygen atom, Z is a methine group or a nitrogen atom. 15 3. The measure according to the alternatives. The compound of claim 2, wherein the active ingredient is a compound of formula 7, wherein X and Y each independently represent a methyl group or a methoxy group and Rr is a methyl group. 4. The measure according to claim 20 A method according to claim 1, characterized in that the active substance is N- (4,6-dimethoxypyrimidinyl) -2-aminoai, ibonyl) -2-hydroxybenzenesiphonamide methylsulfonate with a selective action in wheat crops. ^ 5. The measure according to claims A process as claimed in claim 1, characterized in that the active substance is 2-hydroxy-N- / (4-methoxy-6-methylpyrimidinyl) -2-aminocarbonyl) benzenesulfonamide methylsulfonate with a selective action in wheat crops. 6. The measure according to claim A method according to claim 1, characterized in that the active ingredient is N- (4.6H-dimethyldimethyl) -2Haminocarbonyl) -2-hydroxybenzenesulfonimide methylsulfonate with a selective action in wheat crops. 7. The measure according to claim 8. An agent according to claim 1, characterized in that the active substance is N- (4,6-dimethoxy-1-N-riazinyl-Hiethyl) amino-methyl-1-hydroxybenzenesulfonamide methylsulfonate. the active substance contains 2-hydroxy-N- (4-methoxy-6-methyl-1,3- triazinyl) -2-aminocarbonyl) benzenesulfonamide methylsulfonate. 9. The measure according to claim A process as claimed in claim 1, characterized in that the active ingredient is 45 N- (4,6-dimethyl-11,5-triazinyl) -2-aminocarbonyl) -2-hydroxybenzenesulfonamide methylsulfonate. 10. The measure according to claim A process as claimed in claim 1, characterized in that the active substance is N - ((4,6-dimethoxy-1,3,5-trdazinyl) -2H-methyl / amino-carbonyl) -2-hydroxyibenzenesulfonamide methylsulfonate. 11. The measure according to claim 2. A method as claimed in claim 1, characterized in that the active substance is N, 3, 3, dimethoxyp-irimidinyl [beta] -aminocarbonyl) -2-hydroxybenzenesulfonamide with a selective action in rice and maize crops. 12. The measure according to claim 2. A process as claimed in claim 1, characterized in that the active substance is 2-hydroxy-N- / (4-me1x) Jxy-6-methycH1,3,5-triazinyl) -2-aminocarbonyl) ibenzenesulfonamide with 60 action selective in soybean crops. 13. Process for the preparation of the new o-alkylsulfonyloxy and o-alkylsulfonylaminobenzenesulfonamides of the general formula 7, wherein Q is oxygen or a group of formula NR5, Rx is an alkyl group of 1-4 carbon atoms, a trifluoro-35IB890D 59 methyl group or a phenyl group, Rg represents a hydrogen or chlorine atom, or a methyl group, B "represents a hydrogen or chlorine atom, J14 represents a hydrogen atom or a methyl group, B" represents a methyl group, X represents a group of the formula N ( CH |) j, NHCH3, alkyl group with 1-2 carbon atoms, methdxyl group, alkenes! OxyI group of formula OCHaCH = CH2 or OCH ^ CF3 group, Y is hydrogen or chlorine, methyl or methoxy group, and Z represents a methane group CH, W is a nitrogen atom or a group of the formula CCl, where Y is a chlorine atom, Z is not a nitrogen atom and X is a group of the formula NHCH8 or a methoxy group, when Y is a hydrogen atom, then X is a methyl group and Z - has a meaning other than a nitrogen atom, characterized in that the compound o The aberration 8, in which Q, R 1, Rg, and R3 are substantially as defined above, are substantially reacted with the compound of Formula 9 in which R4, X, Y and Z are as defined above. o, a • & T R NW # zór 1 * tair3 YR, R., usorS Mtzor 6 R ^ S02NHCN <\ R, Y * lZD7 7 hl207 8 N ^ X HhK Z R4 T Mzór 3, 0SCLR Rr ^ SQ, NHCNH U formula 10 uzór8 „uzor 9 R3 SONH Sk ° 7 K« y '' O N_ ^ X UZOT 7 Schernol J M8k + hn4oXi .R / ^ S0aNC0 IM 3 «R4 y mór 9 uzór ff Htor -12 R, Y Cl a ^ fyjco hzot f3 + R. € t, R3 flsaRf 'SqiMH2 h / zor / 4 ^^ QsaRf R3 3aNHCNH- NA "zor 10 IN Cl Schermcrf 3, ci M§t 9 ^ R, SONHCNhKOZ NA« 70 / - tO Cl NaOR6 RijS ^ 0 R3 S0 £ NHCNH ^ OZ m 0R * ^ zar 25 "Schem & f 4 NA128 500 XX HN- (OZ HN0 *. CKOZ * N- ^ HCl N ^ YY formula 16 formula 17 XH * NCH *. CHjNH ^ OT formula 18 Schemo / S <§C CH3 NS0, CH -2-3 CH3 SCLNHCONH- N \ formula 19 IN XCH3 CH3 NS02CH3 CH (PI N_ / 3 ^ SDNHCONI-KÓ) formula 2o OCH, CH, ^^ SOPH * OCHj ^ S0LNHCONH - (Ó "nKcch, heat 21 CH ^ CH, CH, ^^ SO, NHCOHNH ^ O, NN, ** and r" CH3 CH3 ^ NS02CH3 QCH3 ^ SaNHCONH ^ ON CH3 ^ SO ^ HCONH ^ ON ^ CH3 N 3 SQNHCONH- (Ó • ^ N ^ 'CH3 CH' nsoa c SClNHCONH ^ O) h / zor CH3 .NS0, CR £ 6 CH3 _NbU, Ch3 0CH3 SCLNHCONH ^ Ó) formula ^ 7 OCH3 CH3 ^^ SClNHCONH ^ ON M? C? R 28 CH 3 CH 3 g, NSOPF, 5 SO, NHCO NH 3 ON formula 2 9 CH3 0S0mCH, CH3 SONHCONhKoN sodium 30 0CH3 0S04CH3C N ^ CH, CH3 <^ SQ, NHCNH ^ ON M ^ 0CH3 formula 31 ^ £ S0.CH3 (§X * 30 N / OCH, S02NH - ^^ NH- (C » formula 32 N ^ 0CH3128 500 ^ osacH, formula 33 ^ ru ^ SQNH- ^ NH- (§ ^^ 0S02CH, ^^ SO ^ H ^ -nh ^ O ^ J usor3S N CCH3 0S0 £ H £ HCHpHs _ SO / JH- -1— NH- < RTI ID = 0.0 &gt; ** N OCH, osqcHj: HpipH3 © (0N, OCH3SO / JH— ^ NH- ^ rfl Htor 45 CH OSOmCH, ho. OSaCHfH, * CH, OSqpH £ HpHpH, (gT 0 N .OCH, ~ * N \ XH OSOPiCHCHpH, SQNH— ^ NH ^ 43 CH, osach, ^ SaNH ^^ NH-ClJ, 0CHs SANH- ^ "Ch, CH, trzor37 pu -N— <~ 6 OCH, Ni OCH, - • NA - - MO, 39 OCH, osacH, N- .OCK Cl "" SO / lH ^^ - NH ^ U • * <"'a OCH, ^ 0SQCH.Ci SQNH - ^ - NH ^ • N ^ oso2ch3 AA 9 n ^ - same - ^ - NH ^ óS CH,, CH, * vzer A? CH, .OCH. ^ 0S0, CH, AA 0 N ^ a SO ^ - ^ NH ^ ON formula 5 / OCH, .128 500 ^ OSO £ H3 M 0 Cl SQNH - ^ - NH ^ oN. OCH, S2 N ^ .CH, Cl SO ^ H ^ -NH ^ oyCl Hzor 53 N \ ^ .OSO.Hg) SQNH-J ^ NH- (o) OCH. in IM \ «« /•.# OCH. _osa ^ SQNH-MmH ^ Ó .OCH, osa-® CHj ^ SQNH ^ ~ -NH - $$ formula 56 N ^ so2nh ^ nh | ^ i CH, OCH, K ^ sr ^ CH, osa-® ochs © CQN ^ sSaNH ^^ NH- (ON Hzor 58 N ©: psa- © o OCH, CH, SaNH ^ -NH- H »/ gold 59 OCH, oso ^ a L ^ saNH - ^ - ^" rtr "CH qCH 0SO2CH3 Igr o nY CH ^ SaNH ^ -NH ^ a OCH, M? ar ^ 0CH3 -JJSCSPH, C ^ SaNH- ^ NH ^ PCH, ^^ (Pr 62 ¦ * pu PH, osopa £ of o n- / CK saNH- ^ NH- ^ 63 CH, CH, S0.NH NH ^ A1 CH ^ SaNH - ^ - NH ^ ** «" OCH, CH ^ SaNH - ^^^ «* CH, OCH, OSOpHCHCH, 0CHj SONH NT htZOT uzor 67 OCH , 128 50 $ 0S02CHCH £ H3 SO, NH - ^^ NH ^ o) heal 68 N "\" | .OSOpHpHpH, @C 9 Nf SOaNH - ^ - NH - << ^ "» '»N CK -, 0SaCH £ H £ H, (SC ¦ 0 n / osqpHpHPH rN saNH ^ J ^ NH ^ oVci NH * aor 7S rl CK .OCH, ^ VS0tNH (: NH ^ 5 ci oscycH o N_yocHj OCK 0 N_ / 0CH * ^ SaNHCNH - (< ^ l ClOS0CHK OCH, Hzor 73 ° L 9 n ^ oh- feVSO2NHCNH ^ ON Q OSOCH, CH, Clo!% OCH, OSaNHCNH - a oso2ch3 OCH, htzor 75 psac ^ CH, SC ^ NH ^ -NH- CCft "ror 45 N QCH3 OS02CHpHeCKpH3 © CO NJ *» SO2NH ^^ NH ^ O) -Cl NH OSO.CH ^ NHCH4 @ -SO, NHCNH ^ O partition 76 N \ Cl, ci OSCiCH, ^ _ / PN <2S0, NHCNH ^ vzdr /; »OCH3 OSOpW NjX4pH-CHi WSaNHCNH- © Cl * w /» N CH.OSCLCH.- OCH @ ^ S02NHCNH - <^ W »N NfcHU 0S02CH30 OCHs -so2nh (5nh- (5) •" N \ * "» - »NHCH3 osqpn0 och3 <2S0eNHCNH ^ ON // ^ o et n \ oh / c PZGraf. Koszalin A-197 100 A-4 Price 100 il PL PL PL PL PL PL PL

Claims (13)

1. Claims 1. A herbicide containing an active substance, a carrier or a solid or liquid diluent and optionally auxiliary substances, such as surfactants, characterized in that the active substance is a compound of formula 7, wherein Q represents an oxygen atom or a group of formula NR5, Rx represents an alkyl group of 1-4 carbon atoms, a trifluoromethyl group or a phenyl group, R2 represents a hydrogen or chlorine atom, or a methyl group, R3 represents a hydrogen or chlorine atom, R4 represents a hydrogen atom or a methyl group, R 5 is a methyl group. X represents a group of the formula N (CH3) 2, NHCH3, an alkyl group of 1-2 carbon atoms, a methoxy group, an alkenyloxy group of the formula OCH2CH = CH2 or a group of the formula OCH2CF3, Y is a hydrogen or chlorine group, methyl or methoxy group and Z is a methino group, CH, nitrogen atom or a group of formula CCl, where when Y is chlorine, Z is not nitrogen and X is NHCHS or the methoxy group when Y is a hydrogen atom then X is a methyl group and Z is not a nitrogen atom. 2. The measure according to claim A compound according to claim 1, characterized in that the active ingredient is a compound of the formula 7, in which Rj is an alkyl group of 1-3 carbon atoms or a trifluoromethyl group, Q is an oxygen atom, Z is a methine group or a nitrogen atom. 15 3. Measure according to the replacement. The compound of claim 2, wherein the active ingredient is a compound of formula 7, wherein X and Y each independently represent a methyl group or a methoxy group and Rr is a methyl group. twenty 4. The measure according to claim A method according to claim 1, characterized in that the active substance is N- (4,6-dimethoxypyrimidinyl) -2-aminoai, ibonyl) -2-hydroxybenzenesiphonamide methylsulfonate with a selective action in wheat crops. 5. ^ 5. The measure according to claim A process as claimed in claim 1, characterized in that the active substance is 2-hydroxy-N- / (4-methoxy-6-methylpyrimidinyl) -2-aminocarbonyl) benzenesulfonamide methylsulfonate with a selective action in wheat crops. 6. The measure according to claim A method according to claim 1, characterized in that the active ingredient is N- (4.6H-dimethyldimethyl) -2Haminocarbonyl) -2-hydroxybenzenesulfonimide methylsulfonate with a selective action in wheat crops. 7. The measure according to claim A process as claimed in claim 1, characterized in that the active substance is N- (4,6-dimethoxy-1-N-riazinyl-Hiethyl) methylsulfonate, N-hydroxybenzenesulfonamide. 8. The measure according to claim A process as claimed in claim 1, characterized in that the active substance is 2-hydroxy-N- (4-methoxy-6-methyl-1,3- triazinyl) -2-aminocarbonyl) benzenesulfonamide methylsulfonate. 9. The measure according to claim A process as claimed in claim 1, characterized in that the active ingredient is 45 N- (4,6-dimethyl-11,5-triazinyl) -2-aminocarbonyl) -2-hydroxybenzenesulfonamide methylsulfonate. 10. The measure according to claim A process as claimed in claim 1, characterized in that the active substance is N - ((4,6-dimethoxy-1,3,5-trdazinyl) -2H-methyl / amino-carbonyl) -2-hydroxyibenzenesulfonamide methylsulfonate. 11. The measure according to claim 2. A method as claimed in claim 1, characterized in that the active substance is N, 3, 3, dimethoxyp-irimidinyl [beta] -aminocarbonyl) -2-hydroxybenzenesulfonamide with a selective action in rice and maize crops. 12. The measure according to claim 2. A process as claimed in claim 1, characterized in that the active substance is 2-hydroxy-N- / (4-me1x) Jxy-6-methycH1,3,5-triazinyl) -2-aminocarbonyl) ibenzenesulfonamide with 60 action selective in soybean crops. 13. Process for the preparation of the new o-alkylsulfonyloxy and o-alkylsulfonylaminobenzenesulfonamides of the general formula 7, wherein Q is oxygen or a group of formula NR5, Rx is an alkyl group of 1-4 carbon atoms, a trifluoro-35IB890D 59 methyl group or a phenyl group, Rg represents a hydrogen or chlorine atom, or a methyl group, B "represents a hydrogen or chlorine atom, J14 represents a hydrogen atom or a methyl group, B" represents a methyl group, X represents a group of the formula N ( CH |) j, NHCH3, alkyl group with 1-2 carbon atoms, methdxyl group, alkenes! OxyI group of formula OCHaCH = CH2 or OCH ^ CF3 group, Y is hydrogen or chlorine, methyl or methoxy group, and Z represents a methane group CH, W is a nitrogen atom or a group of the formula CCl, where Y is a chlorine atom, Z is not a nitrogen atom and X is a group of the formula NHCH8 or a methoxy group, when Y is a hydrogen atom, then X is a methyl group and Z - has a meaning other than a nitrogen atom, characterized in that the compound o The aberration 8, in which Q, R 1, Rg, and R3 are substantially as defined above, are substantially reacted with the compound of Formula 9 in which R4, X, Y and Z are as defined above. o, a • & T R NW # zór 1 * tair3 YR, R., usorS Mtzor 6 R ^ S02NHCN <\ R, Y * lZD7 7 hl207 8 N ^ X HhK Z R4 T Mzór 3, 0SCLR Rr ^ SQ, NHCNH U formula 10 uzór8 „uzor 9 R3 SONH Sk ° 7 K« y '' O N_ ^ X UZOT 7 Schernol J M8k + hn4oXi .R / ^ S0aNC0 IM 3 «R4 y mór 9 uzór ff Htor -12 R, Y Cl a ^ fyjco hzot f3 + R. € t, R3 flsaRf 'SqiMH2 h / zor / 4 ^^ QsaRf R3 3aNHCNH- NA "zor 10 IN Cl Schermcrf 3, ci M§t 9 ^ R, SONHCNhKOZ NA« 70 / - tO Cl NaOR6 RijS ^ 0 R3 S0 £ NHCNH ^ OZ m 0R * ^ zar 25 "Schem & f 4 NA128 500 XX HN- (OZ HN0 *. CKOZ * N- ^ HCl N ^ YY formula 16 formula 17 XH * NCH *. CHjNH ^ OT formula 18 Schemo / S <§C CH3 NS0, CH -2-3 CH3 SCLNHCONH- N \ formula 19 IN XCH3 CH3 NS02CH3 CH (PI N_ / 3 ^ SDNHCONI-KÓ) formula 2o OCH, CH, ^^ SOPH * OCHj ^ S0LNHCONH - (Ó "nKcch, heat 21 CH ^ CH, CH, ^^ SO, NHCOHNH ^ O, NN, ** and r" CH3 CH3 ^ NS02CH3 QCH3 ^ SaNHCONH ^ ON CH3 ^ SO ^ HCONH ^ ON ^ CH3 N 3 SQNHCONH- (Ó • ^ N ^ 'CH3 CH' nsoa c SClNHCONH ^ O) h / zor CH3 .NS0, CR £ 6 CH3 _NbU, Ch3 0CH3 SCLNHCONH ^ Ó) formula ^ 7 OCH3 CH3 ^^ SClNHCONH ^ ON M? C? R 28 CH 3 CH 3 g, NSOPF, 5 SO, NHCO NH 3 ON formula 2 9 CH3 0S0mCH, CH3 SONHCONhKoN sodium 30 0CH3 0S04CH3C N ^ CH, CH3 <^ SQ, NHCNH ^ ON M ^ 0CH3 formula 31 ^ £ S0.CH3 (§X * 30 N / OCH, S02NH - ^^ NH- (C » formula 32 N ^ 0CH3128 500 ^ osacH, formula 33 ^ ru ^ SQNH- ^ NH- (§ ^^ 0S02CH, ^^ SO ^ H ^ -nh ^ O ^ J usor3S N CCH3 0S0 £ H £ HCHpHs _ SO / JH- -1— NH- < RTI ID = 0.0 &gt; ** N OCH, osqcHj: HpipH3 © (0N, OCH3SO / JH— ^ NH- ^ rfl Htor 45 CH OSOmCH, ho. OSaCHfH, * CH, OSqpH £ HpHpH, (gT 0 N .OCH, ~ * N \ XH OSOPiCHCHpH, SQNH— ^ NH ^ 43 CH, osach, ^ SaNH ^^ NH-ClJ, 0CHs SANH- ^ "Ch, CH, trzor37 pu -N— <~ 6 OCH, Ni OCH, - • NA - - MO, 39 OCH, osacH, N- .OCK Cl "" SO / lH ^^ - NH ^ U • * <"'a OCH, ^ 0SQCH. Ci SQNH - ^ - NH ^ • N ^ oso2ch3 AA 9 n ^ - same - ^ - NH ^ 8S CH,, CH, * vzer A? CH, .OCH. ^ 0S0, CH, AA 0 N ^ a SO ^ - ^ NH ^ ON formula 5 / OCH, .128 500 ^ O SO £ H3 M 0 Cl SQNH - ^ - NH ^ oN. OCH, S2 N ^. CH, Cl SO ^ H ^ -NH ^ oyCl Hzor 53 N \ ^ .OSO.Hg) SQNH-J ^ NH- (o) OCH. in IM \ «« /•.# OCH. _osa ^ SQNH-MmH ^ Ó .OCH, osa-® CHj ^ SQNH ^ ~ -NH - $$ formula 56 N ^ so2nh ^ nh | ^ i CH, OCH, K ^ sr ^ CH, osa-® ochs © CQN ^ sSaNH ^^ NH- (ON Hzor 58 N ©: psa- © o OCH, CH, SaNH ^ -NH- H »/ gold 59 OCH, oso ^ a L ^ saNH - ^ - ^" rtr "CH qCH 0SO2CH3 Igr o nY CH ^ SaNH ^ -NH ^ a OCH, M? ar ^ 0CH3 -JJSCSPH, C ^ SaNH- ^ NH ^ PCH, ^^ (Pr 62 ¦ * pu PH, osopa £ of o n- / CK saNH- ^ NH- ^ 63 CH, CH, S0.NH NH ^ A1 CH ^ SaNH - ^ - NH ^ ** «" OCH, CH ^ SaNH - ^^^ «* CH, OCH, OSOpHCHCH, 0CHj SONH NT htZOT uzor 67 OCH , 128 50 $ 0S02CHCH £ H3 SO, NH - ^^ NH ^ o) heal 68 N "\" |. OSOpHpHpH, @C 9 Nf SOaNH - ^ - NH - << ^ "» '»N CK -, 0SaCH £ H £ H, (SC ¦ 0 n / osqpHpHPH rN saNH ^ J ^ NH ^ oVci NH * aor 7S rl CK .OCH, ^ VS0tNH (: NH ^ 5 ci oscycH o N_yocHj OCK 0 N_ / 0CH * ^ SaNHCNH - (< ^ l ClOS0CHK OCH, Hzor 73 ° L 9 n ^ oh- feVSO2NHCNH ^ ON Q OSOCH, CH, Clo!% OCH, OSaNHCNH - a oso2ch3 OCH, htzor 75 psac ^ CH, SC ^ NH ^ -NH- CCft "ror 45 N QCH3 OS02CHpHeCKpH3 © CO NJ *» SO2NH ^^ NH ^ O) -Cl NH OSO.CH ^ NHCH4 @ -SO, NHCNH ^ O partition 76 N \ Cl, ci OSCiCH, ^ _ / PN <2S0, NHCNH ^ vzdr /; »OCH3 OSOpW NjX4pH-CHi WSaNHCNH- © Cl * w / »N CH. OSCLCH.- OCH @ ^ S02NHCNH - <^ W »N NfcHU 0S02CH30 OCHs -so2nh (5nh- (5) •" N \ * "» - »NHCH3 osqpn0 och3 <2S0eNHCNH ^ ON // ^ o et n \ och / c PZGraf. Koszalin A-197 100 A-4 Price 100 il PL PL PL PL PL PL PL