HRP940888A2 - Certiain 2-(2-substituted benzoyl)-1,3-cyclohexanediones - Google Patents

Description

The technical field to which the invention belongs

This invention relates to the synthesis of organic compounds characterized by biological activity, more specifically, herbicidal activity.

Technical problem

The invention provides certain novel 2-(2-substituted benzoyl)-1,3-cyclohexanediones having excellent general type herbicidal activity.

State of the art

This application is a partial continuation of application Serial no. 587,331, . which was submitted on March 7, 1984, which is again a partial continuation of the application Serial no. 532,869, which was filed on September 16, 1983, which is again a partial continuation of application Serial no. 464,251, which was filed Feb. 9, 1983, which is now abandoned, which is a continuation-in-part of application Serial No. 361,658, which was filed on March 25, and has now been abandoned.

Compounds having the structural formula:

[image]

wherein X may be alkyl, n may be 0, 1 or 2, and R 1 may be phenyl or substituted phenyl are described in Japanese Patent Application 84632-1974 as intermediates for making herbicidal compounds of the formula:

[image]

wherein R 1 , X and n are as defined above and R 2 is alkyl, alkenyl or alkynyl. Specifically recommended herbicidal compounds from the last group are those in which n is 2, X is 5,5-dimethyl, R 2 is allyl and R 1 is phenyl, 4-chlorophenyl or 4-methoxyphenyl.

Precursor intermediates for these three specifically published compounds have no or almost no herbicidal activity.

In contrast, the compounds of the present invention have exceptional herbicidal activity. Applicant's compounds must have a chloro, bromo, iodo or alkoxy substitution in the 2-position of the phenyl group of the compounds to achieve exceptional herbicidal activity. Chlorine is the preferred substituent. The exact reason why such a substitution gives the compound exceptional herbicidal activity is not fully understood.

Description of the solution to the technical problem with implementation examples

This invention relates to certain 2-(2-substituted benzoyl)-cyclohexane-1,3-diones as herbicides. The compounds of this invention have the following structural formula:

[image]

in which:

R and R1 are hydrogen, C1-4 alkyl, preferably methyl or isopropyl, RaOC(C)-, where Ra is Cl-C4 alkyl, most preferably R and R1 are hydrogen: R2 is chlorine, bromine, iodine or Cl-C4 alkoxy, preferably methoxy; most preferably R 2 is chlorine, bromine or methoxy;

R 3 , R 4 and R 5 are independently hydrogen or an aliphatic group, preferably: (1) hydrogen; (2) halogen, preferably chlorine or bromine; (3) C1-C4 alkyl, preferably methyl; (4) C1-C4 alkoxy, preferably methoxy, (5) OCF3: (6) cyano; (7) nitro; (8) C1-C4 haloalkyl, more preferably trufluoromethyl; (9) RbSON- where Rb is C1-C4 alkyl, preferably methyl, Cl-C4 haloalkyl, phenyl, benzyl, -NRdRe where Rd and Re are independently hydrogen or Cl-C4 alkyl; and n is an integer of 0, 1 or 2, preferably 2;

[image]

where Rc is Cl-C4 alkyl (11) RfC(O) where Rf is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, (12) -NRgRh where Rg and Rh are independently hydrogen or Cl-C4 alkyl, or less preferably (13) R 3 and R 4 independently, can form a ring structure with two adjacent carbon atoms of the phenyl ring.

Most preferably R 3 is chlorine, hydrogen, dimethylamino or methoxy. Preferably R4 is hydrogen, chlorine, nitro, SO2CH3, SO2N(CH3)2 or CF3. Preferably, R5 is hydrogen.

Due to tautomerism, the compounds of this invention can have four structural formulas:

[image]

where R, R1, R2, R3, R4 and R5 are as defined above.

The labeled proton on each of the four tautomers is quite labile. These protons are acidic and can be separated by any base so that a salt is obtained that has an anion of the following four resonance forms:

[image]

where R, R1, R2, R3, R4 and R5 are as defined above.

Examples of cations of these bases are such inorganic cations as alkali metals, e.g., lithium, sodium, and potassium, alkaline earth metals, e.g., barium, magnesium, calcium, and strontium, or such organic cations as substituted ammonium, sulfonium, or phosphonium. , where one aliphatic or aromatic group is substituted.

The term "aliphatic group" is used here in a broad sense to cover a large class of organic groups characterized by being derived from (1) acyclic (open chain structure) paraffinic, olefinic and acetylenic hydrocarbons and their derivatives or (2) acyclic compounds . An aliphatic group can have from 1 to 10 carbon atoms.

The term "aromatic group" is used herein in a broad sense as distinguished from an aliphatic group and includes a group derived from (1) compounds having 6 to 20 carbon atoms and characterized by the presence of at least one benzene ring, including monocyclic, bicyclic and polycyclic hydrocarbons and their derivatives and (2) heterocyclic compounds having 5 to 12 carbon atoms that are similar in structure and characterized by having an unsaturated ring structure containing at least one atom other than carbon, such as nitrogen, sulfur and oxygen, and from derivatives of these heterocyclic compounds.

In the above description of the compounds of this invention, alkyl and alkoxy include both straight and branched configurations. string; for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, secbutyl, isobutyl and tert-butyl.

The compounds of this invention and their salts are active herbicides of general type. i.e., they are herbicidally effective against a wide range of plant species. The method for controlling undesirable vegetation of the present invention comprises the application of a herbicidally effective amount of the compounds described above to the surface on which control is desired.

The compounds of the present invention may be made by the following general procedure.

[image]

Molar amounts of dione and substituted benzene cyanide are generally used, together with a slight molar excess of zinc chloride. The two reactants and zinc chloride react in such a solvent as methylene chloride. A slight molar excess of triethylamine is slowly added to the reaction mixture with cooling. The mixture is stirred at room temperature for 5 hours.

The reaction product is processed by conventional techniques.

The substituted benzoyl cyanide described above can be made as described in T.S. Oakwood and C.A. Weisgerber, Organic Synthesis Collected, Vol. III, pp. 122 (1955).

The following example describes the synthesis of a representative compound of this invention.

Examples

2-(2,4-Dicorobenzoyl)-cyclohexane-1,3-dione

[image]

1,3-Cyclohexanedione [11.2 grams (g), 0.1 mole], 20.0 g (0.1 mole) of 2,4-dichlorobenzoylcyanide, and 13.6 g (0.11 mole) of [anhydrous] powdered zinc chloride are added to 100 milliliters (ml) of methylene chloride. Triethylamine (10.1 g, 0.12 mol) was added slowly with cooling. The reaction mixture was stirred at room temperature for 5 hours and then poured into 2N hydrochloric acid. The aqueous phase was discarded and the organic phase was washed with 150 ml of 5% Na2CO3 for four times. The aqueous liquids from the evaporation are combined and acidified with HCl, extracted with methylene chloride, dried and concentrated to give 25.3 g of crude product. The crude product is dissolved in ether and mixed with 250 ml of 5% copper (II) acetate. The resulting copper salt is filtered, washed with ether and mixed with 6N hydrochloric acid to break up the salt.The extract is washed with ether to give 22.15 grams of the desired product, mp 138-140°C (77.7% yield). The structure was confirmed by instrumental analysis.

The following is a table of certain selected compounds that can be made according to the procedure described here. Each connection is given a number and these numbers are used in the rest of the application.

TABLE I

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[image] [image]

*= Made in the example.

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Tests for the evaluation of herbicidal activity

As mentioned earlier, the compounds of this application produced in the manner described above are phytotoxic compounds that are useful and valuable for the control of various plant species. Selected compounds from this invention were tested as herbicides in the following manner.

Test for herbicidal activity before emergence

On the day before the treatment, the seeds of eight different weed species are planted in clayey sandy soil in individual rows, using one species per row along the width of the vase. The seeds of the plants used were green turnip (FT) (Setaria viridis), water grass (WG) (Echinochloa . crusgalli), wild oats (WO) (Avena fatua), one-year sedum (AMG) (Impoea lacunosa), kadiva (VL) ( Abutilon theophrasti), Indian mustard. (MD) (Brassica juncea), red root starch (PW) (Amarthaus retroflexus) or curly greens (CD) (Rumex crispus) and yellow nut (YNG) (Cyperus esculentus). Plant enough seeds to get about 20 to 40 seeds per row, after germination, depending on the size of the plants.

Using an analytical balance, 600 mg of the compound to be tested is weighed onto a piece of glass weighing paper. The paper and compound are placed in a 60 ml wide-necked bottle and dissolved in 45 ml of acetone or some substituted solvent.

18 ml of this solution is transferred to a 60 ml bottle with a wide mouth and diluted with 22 ml of a mixture of water and acetone (19:1) containing enough polyoxyethylene sorbitan monolaurate emulsifier to obtain a final solution of 0.5% (v/v) . The solution is then sprayed onto the planted vase on a linear spray table calibrated to deliver 748 L/ha. The application rate is 4.48 Kg/ha.

After treatment, the vases are placed in a glass garden at a temperature of 21.1 to 26.6°C and irrigated by spraying. Two weeks after treatment, the degree of damage or control is determined by comparing it with untreated control plants of the same age. Record a damage estimate from 0 to 100% for each species as a percentage of control where 0% means no damage and 100% represents complete control.

The test results are shown in the following Table II.

TABLE II

[image] [image]

- The species did not sprout for some reason.

A blank indicates that the weed has not been tested.

Test for herbicidal activity after emergence

This test was performed identically to the test procedure in the postemergence herbicide test, except that seeds of eight different weed species were planted 1012 days before treatment. Also, the watering of treated vases is limited to the surface of the land and not to the leaves of the tested plants.

The results of post-emergence herbicidal activity testing are listed in Table III.

TABLE III

Herbicidal activity after emergence

Application rate -4.48 kg/ha

[image] [image]

Testing pre-emergence herbicidal activity against multiple weeds

Several compounds were evaluated at 2.24 kg/ha for preemergence activity against a number of weed species.

The procedure was essentially similar to the preemergence herbicidal activity assay described above except that 300 mg of the compound was measured. which is being tested, and the application rate was 375 L/ha.

Red root starch (PW) and curly greens (CD) were eliminated from this test, and the following weed species were added:

Grasses: Bromus tectorum (DB)

annual rice grass Lolium multiflorum (ARG)

orange sorghum Sorghum bicolor (SHC)

sesbania hemp Sesbania exaltata (SESB)

nightshade Solanium sp. (SP)

dike Xattiium sp. (CB)

The results are presented in Table IV.

TABLE IV

Testing preemergence herbicidal activity on multiple weeds

[image]

The compounds of the present invention are useful as herbicides, especially as pre-emergent herbicides, and can be applied in different ways at different concentrations. In practice, the compounds defined here are formulated into herbicidal mixtures, by mixing, in herbicidally effective amounts with adjuvants and carriers, which are normally used to facilitate the dispersion of active components for agricultural use, recognizing the fact that the formulation and method of application of the toxicant can affect the activity of the material in a given application. Thus, these active herbicidal compounds can be formulated as granules of relatively large substance sizes, as wettable powders, as emulsifiable concentrates, as powders, as solutions, or as any of several other types of formulations, depending on the desired method of application. The best formulations for pre-emergent herbicide applications are wettable powders, emulsifiable concentrates and granules. These formulations may contain as little as about . 0.5% to as much as about 95% or more by weight of the active component. The herbicidally effective amount depends on the nature of the seed or plant to be controlled and the application rate varies from about 0.1 to about 10 pounds per acre.

Wettable powders are in the form of finely dispersed substances that are easily dispersed in water or other dispersants. The dust that is wet is ultimately applied to land either as a dry dust or as a dispersion in water or another liquid. Typical carriers for wetting powders include fuller's earth, kaolin earth; silicon dioxide and other organic or inorganic solvents that are easy to urinate. Wetting powders are normally formulated to contain about 5% to about 95% of the active component and usually also contain a small amount of wetting, dispersing or emulsifying agent to facilitate wetting and dispersing.

Concentrates that emulsifiers are homogeneous liquid mixtures that are dispersed in water or other dispersants and may consist of an active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier such as . xylene, heavy aromatic naphthalene, isophorone and other non-volatile organic solvents. For herbicidal use, these concentrates are dispersed in water or other liquid carriers and applied as a spray to the area to be treated. The percentage by weight of the basic active component can vary depending on the way in which the mixture is to be applied, but it usually contains about 0.5% to 95% of the active component by weight of the herbicidal mixture.

Formulations in the form of granules, in which the toxicant is applied to relatively coarse particles, are usually applied without dilution to the area where vegetation control is to be achieved. Typical carriers for granular formulations include sand, fuller's earth, bentonite soils, vermiculite, perlite, and other organic and inorganic materials that absorb or can be coated with the toxicant. Formulations in the form of granules are normally obtained so that they contain about 5% to about 25% of active components, which may also include surface-active agents such as heavy aromatic oils, kerosene or other oil fractions, or vegetable oils; and/or binding agents such as destrins, glue or synthetic resins.

Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, for example, alkyl and alkylaryl sulfonates and sulfates and their sodium salts; polyhydroxyl alcohols; and other types of surfactants, many of which are commercially available. Surfactants, when used, normally represent from 0.1 to 15% by weight of the herbicidal mixture.

Powders, which are mixtures (mixtures), active components with finely divided solid material, such as talc, clay, flour and other organic and inorganic solids, which act as dispersants and carriers for toxicants, are useful formulations for application by incorporation into the soil .

Pastes, which are homogeneous suspensions of finely divided solid toxicant in a liquid carrier such as water or oil, are used for specific purposes. These formulations normally contain about 5% to about 95% of the active component by weight, and may also contain small amounts of wetting, dispersing or emulsifying agents to facilitate dispersion. For application, the paste is normally diluted and applied as a spray to the area to be treated.

Other useful formulations for herbicidal applications include ordinary solutions of the active component in a dispersant in which it is completely dissolved at the desired concentration. Dispersants can be acetone, alkylated naphthalene, xylene and other organic solvents. Pressurized sprays, typical aerosols, where the active component is dispersed in finely divided form as a result of evaporation of the carrier solvent, low boiling point, such as freons, which can also be used.

Phytotoxic mixtures from this invention are applied to plants in the usual way. Thus, powder and liquid compositions can be applied to plants using powder sprayers, lever sprayers, and handheld sprayers. The mixtures can also be applied from airplanes as a dust or spray since they are effective in small doses. In order to modify the growth control or seed germination or to induce plant growth from seed, as a typical example, powder and liquid mixtures are applied to the soil in accordance with conventional methods and distributed into the soil to a depth of at least 1/2 inch below the surface. land. It is not necessary to mix the phytotoxic mixture with soil particles, since these mixtures can also be applied only by spraying or spraying on the soil surface. The phytotoxic compositions of the present invention can also be applied by addition to the irrigation water supplied to the field to be treated. This application procedure enables the penetration of the mixture into the soil since the water is absorbed in the soil. Powder mixtures, granule mixtures, or liquid formulations applied to the soil surface can be distributed below the soil surface by conventional means, such as discing, bagging, or mixing operations.

The phytotoxic preparations of this invention may also contain other additives, for example, fertilizers and other herbicides, pesticides and the like, used in addition to or in combination with any of the additives described above. Other phytotoxic compounds useful in combination with the compounds described above include, for example, such analides as: 2-benzothiazol-2-yloxy-N-methyl-acetanilide, 2-chloro-2',6'-dimethyl-N -(n-propylethyl), acatanilide, 2-chloro-2',6'-diethyl'-N(butoxy methyl)acetanilide, 2,4-dichlorophenoxyacetic acid, 2,4,5-trichlorophenoxyacetic acid, 2-methyl-4 -chlorophenoxy acetic acid and their salts, esters and amides; triazine derivatives, such as 2,4-his (3-methoxypropyl-amino)-6-methylthio-s-triazine, 2-chloro-4-ethylamino-6-isopropylaminos-triazine and 2-ethylamino-4-isopropyl-amino -6-methylmercapto-s-triazine; carbamide derivatives, such as 3-(3,5-dichlorophenyl)-1,1-dimethylcarbamide and 3-(p-chlorophenyl)-1,1-dimethylcarbamide; and such acetamides as N,N-diallyl-alpha-chloroacetamide and the like; such benzoic acids as 3-amino-2,5-dichlorobenzoic acid; thiocarbamates such as S-(1,1-dimethylbenzyl)piperidine 1-carbotioate, 3-(4-chlorophenyl)-methyl diethylcarbotioate, ethyl-1-hexahydro-1,4-azepine-1-carbotioate, S-ethyl-hexahydro -1-azepine-1-carbothioate, S-propyl N,N-diopropylthiocarbamate, S-ethyl N,N-dipropylthiocarbamate, S-ethyl cyclohexylethylthiocarbamate, S-ethyl-hexahydro-1H-azepine-1-carbothioate and the like; anilines such as 4-(methylsulfonyl)-2,6-dinitro-N,N-substituted aniline, 4-trifluoromethyl-2,6-dinitro-N,N-di-n-propylaniline, 4-trifluoromethyl-2,6 -dinitro-N-ethyl-N-butylaniline, 2-/4-(2,4-dichlorophenoxy)phenox propanoic acid, 2-/1-(ethoxyimino)-butyl/-5-/2-ethylthio)propyl3-hydroxy- 2-cyclohexan-1-one, (±)-butyl-2-/4/(5-trifluoromethyl)2-pyridinyl)oxy/phenoxy/propanate, sodium 5-/2-chloro-4-(tri-fluoromethyl)phenoxy /-2-nitrobenzoate, 3-isopropyl-1H-2,1,3-benzothiadiazine-4-(3H)-one-2,2-dioxide and 4-amino-6-tert-butyl-3-(methylthio)- s-triazin-5(4H)-one or M-amino-6-(1,1-dimethyl)-3-(methyllithio)-1,2,4-triazin-5(4H)-one) and s-( 0,0-diisopropyl)-benzenesulfonamide. Fertilizers useful in combination with active ingredients include, for example, ammonium nitrate, carbamide and superphosphate. Other useful additions include materials in which plant organisms take root and grow such as manure, humus, sand and the like.

Claims (46)

1. Compound of the structural formula [image] indicated by the fact that they are R and Rl are hydrogen, Cl-C4alkyl, RaOC (O)-, where Ra is Cl-C4alkyl, R 2 is chlorine, bromine, iodine or C 1 -C 4 alkoxy, and R3 and R4 and R5 are each independently (1) hydrogen, (2) halogen, (3) C1-C4 alkyl, (4) C1-C4 alkoxy, (5) nitro, (6) C1-C4 haloalkyl, (7) RbSOn- where Rb is Cl-C4alkyl and n is an integer of 0, 1 or 2, (8) [image] where Rc is Cl-C4alkyl, or (9) R3 and R4 together may form a ring structure together with two adjacent carbon atoms of the phenyl ring, as well as its salts provided that they are compounds having the structural formula [image] in which they are R and R1 are hydrogen or Cl-C4alkyl, R 2 is chlorine, bromine, or iodine, R3 is hydrogen, or halogen, and R 4 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro or trifluoromethyl excluded. 2. Compounds according to claim 1, characterized in that R and R1 are hydrogen or Cl-C4alkyl; R2 is chlorine, bromine, iodine or C1-C4 alkoxy; R 3 and R 4 are each independently hydrogen, halogen, C 1 -C 4 alkoxy, nitro, C 1 -C 4 haloalkyl, RbSOn where Rb is C 1 -C 4 alkyl; and n is an integer of 0, 1 or 2; RcC(O)NH- where Rc is Cl-C4alkyl; R5 is hydrogen, and its salts. 3. Compounds according to claim 1, characterized in that R and R1 are hydrogen or methyl; R 2 is chlorine, bromine or methoxy; R 3 is hydrogen, chlorine, dimethylamino or methoxy; R4 is hydrogen, chlorine, nitro, RbSOn where Rb is Cl-C4alkyl and n is 0 or 2; SO2N(CH3)2 or CF3; and R5 is hydrogen, and its salts. 4. Compounds according to claim 3, characterized in that R3 is substituted in the 3-position, R4 is substituted in the 4-position and R5 is substituted in the 5- or 6-position, and their salts. 5. Compounds according to claim 3, characterized in that R and R1 are hydrogen; R 2 is chlorine or methoxy; R3 is hydrogen, 3-chloro, 3-methoxy, 3-ethoxy, 3-n-propoxy, 4-methoxy or 3-dimethylamino and R4 is 4-chloro, 4-bromo, 4-CH3SO2-, 4-C2H5SO2 -; and R5 hydrogen and their salts. 6. Salts of compounds according to claim 2, characterized in that R2 is chlorine. 7. Salts of compounds according to claim 1, characterized in that R is methyl, R1 is methyl, R2 is chlorine, R3 is hydrogen, R4 is hydrogen and R5 is 6-chloro. 8. Salts of compounds according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is hydrogen and R5 is 6-chloro. 9. Salts of compounds according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-chloro and R5 is hydrogen. 10. Salts of compounds according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chloro, R4 is hydrogen and R5 is 6-chloro. 11. Salts of compounds according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is hydrogen and R5 is 5-trifluoromethyl. 12. Salts of compounds according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chloro, R4 is 4-chloro and R5 is hydrogen. 13. Salts of compounds according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chloro, R4 is 4-methoxy and R5 is hydrogen. 14. Salts of compounds according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is bromine and R5 is hydrogen. 15. A compound according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chloro, R4 is nC3H7SO2- and R5 is hydrogen and its salts. 16. Salts of compounds according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-chloro and R5 is hydrogen. 17. Compound according to claim 1, characterized in that R is isopropyl, R1 is hydrogen, R2 is chlorine, R3 is 3-CH3, R4 is 4-CH3SO2 and R5 is hydrogen and its salts. 18. A compound according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-CH3SO2 and R5 is hydrogen and its salts. 19. Salts according to claim 12, characterized in that they are sodium, isopropylamine, triethylamine and potassium salts. 20. The method of controlling unwanted vegetation, characterized by the fact that it includes the application, in the area where the control is to be carried out, of a herbicidally effective amount of the compound of the formula [image] in which they are R and Rl are hydrogen, Cl-C4alkyl, RaOC (O)-, where Ra is Cl-C4alkyl, R 2 is chlorine, bromine, iodine or C 1 -C 4 alkoxy, and R 3 and R 4 and R 5 are each independently (1) hydrogen, (2) halogen, (3) C 1 -C 4 alkyl , (4) C 1 -C 4 alkoxy, (5) nitro, (6) C 1 -C 4 haloalkyl, (7) RbSOn- where Rb is Cl-C4alkyl and n is an integer of 0, 1 or 2, (8) [image] where Rc is Cl-C4alkyl, or (9) R3 and R4 together may form a ring structure together with two adjacent carbon atoms of the phenyl ring, or one of its salts provided that they are compounds having the structural formula [image] in which they are R and Rl are hydrogen or Cl-C4alkyl, R 2 is chlorine, bromine, or iodine, R3 is hydrogen, or halogen, and R 4 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro or trifluoro methyl excluded. 21. The method according to claim 20, characterized in that R and R1 are hydrogen or Cl-C4alkyl; R 2 is chlorine, bromine, iodine or C 1 -C 4 alkoxy: R 3 and R 4 are each independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, C 1 -C 4 haloalkyl, RbSOn where Rb is C 1 -C 4 alkyl; and n is an integer of 0, 1 or 2; RcC(O)NH- where Rc is Cl-C4alkyl; R 5 is hydrogen; and its salts. 22. The method according to claim 20, characterized in that R and R1 are hydrogen or methyl; R 2 is chlorine, bromine or methoxy; R 3 is hydrogen, chlorine or methoxy; R4 is hydrogen, chlorine, nitro, RbSOn where Rb is Cl-C4alkyl and n is 0 or 2; SO2N(CH3)2 or CF3; and R5 is hydrogen, and its salts. 23. The method according to claim 22, characterized in that R3 is substituted in the 3-position, R4 is substituted in the 4-position and R5 is substituted in the 5- or 6-position and their salts. 24. The method according to claim 22, characterized in that R and R1 are hydrogen; R 2 is chlorine or methoxy; R 3 is hydrogen, 3-chloro, 3-methoxy, 3-ethoxy, 3-n-propoxy, 4-methoxy or 3-dimethylamino; R4 is 4-chloro, 4-bromo, 4-CH3SO2, 4-C2H5SO2- or 4-CH3SO2; and R5 is hydrogen and their salts. 25. The method according to claim 24, characterized in that R2 is chlorine and its salts. 26. The method according to claim 20, indicated by the fact that the salt of the compound in which R is methyl, R1 is methyl, R2 is chlorine, R3 is hydrogen, and R5 is 6-chloro is used. 27. The method according to claim 20, characterized in that the salt of the compound in which R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is hydrogen, R5 is 6-chloro is used. 28. The method according to claim 20, characterized in that the salt of the compound in which R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-chloro and R5 is hydrogen is used. 29. The method according to claim 20, characterized in that the salt of the compound in which R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chloro, R4 is hydrogen and R5 is 6-chloro is used. 30. The method according to claim 20, characterized in that the salt of the compound in which R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is hydrogen and R5 is 5-trifluoromethyl is used. 31. The method according to claim 20, characterized in that the salt of the compound in which R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chloro, R4 is 4-chloro, R5 is hydrogen is used. 32. The method according to claim 20, characterized in that the salt of the compound in which R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chloro, R4 is 4-methoxy, R5 is hydrogen is applied. 33. The method according to claim 20, characterized in that the salt of the compound in which R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is bromine, R5 is hydrogen is used. 34. The method according to claim 20, characterized in that the salt of the compound in which R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chloro, R4 is nC3H7SO2- and R5 is hydrogen and its salts is used. 35. Process according to claim 20, characterized in that R is isopropyl, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-chloro and R5 is hydrogen and its salts. 36. Process according to claim 20, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-CH3O, R4 is 4-CH3SO2 and R5 is hydrogen and its salts. 37. Process according to claim 20, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-CH3SO2 and R5 is hydrogen and its salts. 38. The method according to claim 20, characterized in that the salts are sodium, isopropylamine, triethylamine and potassium salts. 39. A compound according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-C2H5S, R4 is 4-C2H5SO2 and R5 is hydrogen and its salts. 40. A compound according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-methoxy, R4 is 4-C2H5SO2 and R5 is hydrogen and its salts. 41. A compound according to claim 1, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chloro, R4 is 4-n-C3H7SO2- and R5 is hydrogen and its salts. 42. The process according to claim 20, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-C2H5S, R4 is 4-C3H7SO2 and R5 is hydrogen and its salts. 43. Process according to claim 20, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-methoxy, R4 is 4-CH3SO2 and R5 is hydrogen and its salts. 44. The method according to claim 20, characterized in that R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chloro, R4 is 4-n-C3H7SO2- and R5 is hydrogen and its salts. 45. Herbicidal preparation, characterized in that it contains the compound according to claim 18 or one of its salts and inert bases for it. 46. The method of controlling unwanted vegetation, characterized by the fact that it includes the application, in the area where the control is to be carried out, of a herbicidally effective amount of the compound according to claim 18 or one of its salts and an inert substrate for it.