CH683341A5 - Substituted Phenylsulfonyltriazinylharnstoffe, their salts and means for stimulation and suppression of plant growth on the basis thereof. - Google Patents

Abstract

The invention relates to substituted phenylsulphonyltriazinylureas and to their salts. According to the invention, the compounds have the general formula: <IMAGE> where R1 is Cl, NO2 or COOCH3; R2 is H or Cl; R3 is H or CH3; R4 is CH3, C2H5, C6H5 or 2-ClC6H4 and where X does not exist or is represented by K, Na or <IMAGE> . The invention applies especially to organic chemistry and, in particular, to the treatment of plants.

Description

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CH 683 341 A5

description

Technical field

The present invention relates to new compounds substituted phenylsulfonyltriazinyl ureas, their salts and agents for stimulating and inhibiting plant growth on the basis thereof.

State of the art

An important problem in agriculture is increasing the harvest. For this purpose, growth stimulants and herbicides are used.

The simultaneous use of the herbicides and the growth stimulant creates certain difficulties, since the specifics of their effects depend on the type of agricultural crop.

Various compounds are known which have herbicidal activity. For example, a compound 1- (2-chlorobensensulphonyl) -3- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea is known. The preparation based on the compound mentioned is used in agriculture to protect wheat, barley, rye, oat and linseed from weeds (US, A, 4,127,405).

Also known are substances which, in addition to the herbicidal activity, have the properties of the growth regulator of plants. The effects of these substances are usually accompanied by a retarding, growth-inhibiting or formative effect. Such compounds include arylsulfonylurea derivatives of the general formula:

n (ch3) 2

so2nhcohh

<ÖCH-

where R is Ci, CO2CH3, CH3.

Such compounds show herbicidal properties in a dose of 60 to 400 g / ha and have the retarding growth-inhibiting or formative effect (US, A, 4,231,784).

The known compounds suppress the growth of the crop plants.

Presentation of the invention

The registered connections are new and not described in the specialist literature.

The invention has for its object to develop new compounds which have a growth-stimulating activity with a simultaneous herbicidal effect.

The object was achieved in that new compounds, substituted phenylsulfonyltriazinylureas and their salts of the general formula:

r '

n (ch3) 2

vso2nhconh

Ond

0-n = cr? A4

wherein

R1 for Ci, NOa, COOCH3 r2 for H, CI R3 for H, CH3

Ri stands for CH3, C2H5, 06H5, 06H4CI-2 and x is missing or

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CH 683 341 A5

", K, Na, hh ^ cp |

^ OjH ^ OH

means to be proposed.

The compounds according to the invention have growth-stimulating and herbicidal activity. The agent for stimulating and suppressing plant growth, which provides an active ingredient and a diluent, contains, according to the invention, the compounds according to the invention, substituted phenylsulfonyltriazinylureas or their salts. The claimed agent according to the invention preferably contains 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxy-1,3,5-triazin-2-yl) urea or its potassium, sodium or diethylethanolammonium salt as active ingredient following formula:

k (oh3j2

A

S02iraC0NH-

—U-

N

/ GH-0-n = c;

wherein

X is missing or

X.K, Na, hh - c_h_

\

c2h40h means.

According to the invention, the claimed agent can preferably be 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylideniminooxy-1,3,5-triazin-2-yl] urea or its potassium as active ingredient -, sodium or diethyl ethanol ammonium salt of the following formula:

Cl

? (ch3) 2

N

'SO ^ hcomh

N

N

o-n = cC 3

2H5

X

wherein

X is missing or

--C2H5 X = K, Na, hn - oghj

X <WH

means included.

The claimed agents have a high activity and are used to stimulate and inhibit plant growth.

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Way of carrying out the invention

The new compounds according to the invention, substituted phenylsuifonyltriazinylureas, are stable white crystalline substances which are poorly soluble in water and in organic solvents.

The substituted phenylsulfonyltriazinylureas according to the invention are prepared by reacting the substituted benzenesulfonyl isocyanates with substituted 2-amino-1,3,5-triazines in which

R1 for Ci, NO2, COOCHa;

R2 for H, Ci;

R3 for H, CH3;

R4 represents CH3, C2H5, C6H5, C6H4CI-2.

The starting components are taken at a weight ratio of 1: 1. The process is carried out in an organic solvent (benzene, xylene, toluene, acetonitrile, tetrahydrofuran) in the presence of catalytic amounts of tetramethylethylenediamine at a temperature of 50 to 60 ° C. within 2 hours. Then the temperature of the reaction mass is reduced to 20 ° C and mixed for a further 2 hours until the reaction is complete. The residue is filtered off, washed with a solvent in which the reaction is carried out, and dried.

The compounds according to the invention can also be obtained by reacting substituted arylsulfone amide with chlorosulfonyl isocyanate and substituted 2-amino-1,3,5-triazine in an organic solvent (toluene, xylene) at a temperature of 60 to 70 ° C. within 3 hours will.

R

2nd

^ 0-ÎÎ = CR3s4

N (CH3) a r

sognhconh

1

»

wherein

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CH 683 341 A5

R1 for Cl, NO2, COOCHs;

R2 for H, Cl;

R3 for H, CH3;

R4 represents CH3, C2H5, C6H5, C6H4CI-2.

The structures of the synthesized substituted phenylsulfonyltriazine ureas were proven by the methods of element analysis, IR and ESR'-H spectroscopy. The IR spectra were recorded on the «PYE UNICAM» device in KBr tablets. The ESR'-H spectra are recorded on the device «WM-250» in deuteroacetone using tetramethylsilane as the internal standard.

As an example, the ESR'-H spectrum of 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylidiminooxy-1,3,5-triazin-2-yl) urea is given in the signals the protons of the isopropylidene group at 2.04 ppm (singlet), 6H of the dimethylamine group at 3.11 ppm (doublet), 6H signals of the protons of the phenyl ring would be detected at 7.5-7.7 ppm (multiplet), 3H and 8.22 ppm (double doublet) H6 detected. Proton signals from two NH groups are observed at 9.33 ppm (singlet) 1H and 13.59 ppm (singlet) 1H. The counting of the signals mentioned was proven by means of the synthesized sulfonylurea, labeled with isotope 15N after the nitrogen atom of the sulfamide group. The spin-spin splitting of the 15N-H signal at 13.59 ppm, equal to 90 Hz, made it possible to count the resonance signal mentioned to the hydrogen of the sulfamide group.

Salts of the substituted phenylsulfonyltriazinylureas are crystalline substances which are soluble in water and in several organic solvents, for example in alcohols, glycols and sulfoxides.

The claimed salts are prepared by reacting the substituted phenylsulfonyltriazinyl ureas with an alkali metal hydroxide (potassium or sodium) or with diethyl ethanolamine in a mass ratio of 1: 1.1 in a medium of an organic solvent (alcohols) or in water at between 35 and 40 ° C temperature within 3 hours ago. The structure of the claimed salts has been demonstrated using ESR'-H and IR spectroscopy methods.

In the ESR'-H spectrum Na salts of 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylidene-iminooxi-1,3,5-triazin-2-yl) urea, recorded in deuteroacetone, the proton signal disappears at N-1 atom. Oil-like compounds are formed when the substituted ureas according to the invention are reacted with fatty amines. The elemental analysis, for example for the product of the reaction of diethylethanolamine with the substituted urea mentioned above, shows the formation of an adduct between the components to be reacted in a ratio of 1: 1.

In the ESR'-H spectrum of this adduct, recorded in deuteroacetone, there are no signals from the protons of both amide protons, which testifies to the formation of a salt-like compound.

The NMR H1 spectra of the substituted urea mentioned according to the invention and its sodium and diethylethanolamine salt are given below:

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CH 683 341 A5

'so,

jÌhcoSH - ^ "^

(CH,)

3 2

0-N = G (CHj) £ 2! ^, 03 "doublet,

f ^ gr

'SOgN-OONH- ^ NÄ

4th

■ K

«0 H3) 2

4th

CH

3rd

ON-C

/ CH5

\

CH.

5.11 Duplet, ïï (ch3) 2

7.69-8.13 multiplet, Ar

10.69 ßingulott

HH

15 * 61 singlet 2

m

S: 2.05 singlet, C

CH, ■ CH,

3.08 doublet, N (CH3) 2 7.58-8.03 multiplet, Ar 9.13 singlet, NH

8: 1.18 singlet CH3 (C2Hs)

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CH 683 341 A5

oil

Kch3) 2

s02nhc0nh

'ö-n-c (ch5) 2

(C2H5) 2NCH2CH20H

2.02 doublet, C (CH3) 2 (Het)

2.98 Quartet, CH2 (C2H5)

3.15 doublet, N (CH3) 2 3.8 multiplet, CH2CH2 6.35 singlet, OH 7.5-8.1 multiplet, Ar

The NMR 1H spectra are recorded on a «WM-250» device with a frequency for H + 250.13 MHz.

Thanks to the information given, the following structure can be assumed for the salt according to the invention:

All claimed compounds have plant growth activity.

The claimed compounds are active ingredients of the agent for stimulating and inhibiting plant growth. The activity of the claimed compounds and the agent based on them was investigated on plants in laboratory and field tests.

The claimed compounds have an ability to accelerate the development of several crop plants in the youth stage of organogenesis, which entails the formation of larger young plants, that is to say the compounds claimed first selectively stimulate the crop plants and at the same time inhibit growth and weed development.

The biological tests of the compounds according to the invention on cereals (for example wheat, barley), maize and cotton were investigated and it was demonstrated that the compounds according to the invention are superior to the known glean preparations, gibberellin and atrazine in terms of herbicide and plant growth activity.

Gibberellin causes elongation of the stem, does not have a positive influence on the biomass of the aerial part of the plant; as a result, they were formed as thin and stored. Atrazine works in a similar way with stressed compounds, but in doses exceeding 10 to 25 times.

All claimed compounds are not very toxic, LD50 intramuscularly in white mice is> 5000 mg / kg. The preparation based on the substances according to the invention can be used in the form of wettable powders, granules and solutions. The claimed agent is intended for the treatment of both green plants and soil by spraying, powdering, swelling and pilling of the seeds.

For a better understanding of the present invention, the following examples are given for the preparation of the compounds according to the invention, tests of their activity and their use.

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example 1

1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxy-1,3,5-triazin-2-yl) urea (compound 1).

A suspension of 9.57 g (0.05 mol) of 2-chlorobenzenesulfonamide and 0.3 ml of tetramethylethylenediamine in 100 ml of o-xylene is added to 7.1 g (0.05 mol) of chlorosulfonyl isocyanate at a temperature of 20 ° C. to. The reaction mixture is heated within 3 hours at a temperature of 95 to 100 ° C, cooled and added 11.2 g (0.05 mol) of 2-amino-4-dimethylamino-6-isopropylideniminooxy-1,3,5- tria-zin added; the mixture is heated in the course of 3 hours at a temperature of 50 to 60 ° C, cooled, the residue is filtered off and a compound 1 is obtained in an amount of 17.0 g (80%) of melting point 184-186 ° C (from acetonitrile).

Found,%: C 41.94; H 4.34; N 22.81; CI 6.96; S 8.14; C15H18CIN7O4S.

Calculated,%: C 42.11; H 4.24; N 22.92; Eq 8.28; S 7.50.

Example 2

1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxy-1,3,5-triazin-2-yl) urea (compound 1).

A suspension of 19.0 g (0.09 mol) of 2-amino-4-dimethylamino-6-isopropylideneiminooxy-1,3,5-triazine in 50 ml of benzene, heated to a temperature of 60 ° C., is added gradually add a solution of 21.7 g (0.1 mol) of 2-chlorobenzenesulfonyl isocyanate in 100 ml of benzene. The reaction mixture is mixed within 3 hours at a temperature of 60 to 70 ° C and then for a further 2 hours at room temperature. The residue is filtered off, washed with benzene, dried and 36.5 g (95%) of 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxy-1,3,5-triazine-2) are obtained -yl) urea with a melting point of 184-186 ° C. The data from the elementary analysis are similar to those given in Example 1.

Example 3

1- (2-Chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazin-2-yl] urea (Compound 2).

1 drop of tetramethylethylenediamine is heated to a suspension of 2.06 g (0.0029 mol) of 2-amino-4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazine in 40 ml of dry benzene the mixture to a temperature of 50 to 60 ° C and adds 2.15 g (0.0099 mol) of 2-chlorobenzenesulfonyl isocyanate. The reaction mixture is mixed within 2 hours at a temperature of 60 ° C. and for a further 2 hours at a temperature of 20 ° C., the residue is filtered off and 4.0 g (95%) of compound 2 with a melting point of 172-173 ° are obtained C (with decomposition).

Found,%: C 43.22; H 4.68; N 22.31; CI 7.81; S 7.46; C16H20CIN7O4S.

Calculated,%: C 43.49; H 4.56; N 22.19; CI 8.02; S 7.25.

Example 4

1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxy-1,3,5-triazin-2-yI-) urea (compound 3).

Similar to Example 1, 2-chlorobenzenesulfonyl isocyanate and 2-amino-4-dimethyl-amino-6-benzylideniminooxi-1,3,5-triazine give the above-mentioned urea with a melting point of 178 ° C .; the yield is quantitative.

Found,%: C 47.67; H 4.05; N 20.65; CI 7.61; S 6.75; C19H18CI1N7O4S.

Calculated,%: C 47.95; H 3.81; N 20.65; CI 7.45; S 6.73.

Example 5

1- (2-Chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (2-chloro) benzylideneiminooxi-1,3,5-triazin-2-yl] urea (Compound 4).

Similar to Example 2, 2-chlorobenzenesulfonyl isocyanate and 2-amino-4-dimethylamino-6- (2-chloro) benzylidiminooxi-1,3,5-triazine give the above-mentioned urea with a melting point of 167-168 ° C .; the yield is 96.5%.

Found,%: C 44.80; H 3.64; N 18.94: CI 13.76; S 6.34; Ci9H17Cl2N704S.

Calculated,%: C 44.71; H 3.36; N 19.22; CI 13.89; S 6.28.

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CH 683 341 A5

Example 6

1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxy-1,3,5-triazin-2-yl) urea (compound 5).

Analogously to that described in Example 2, 2-nitrobenzenesulfonyl isocyanate and 2-amino-4-dimethylamino-6-isopropylideneiminooxi-1,3,5-triazine give the above-mentioned urea with a melting point of 190 ° C .; the yield is 88%.

Found,%: C 40.87; H 4.21; N 25.35; S 7.46; CisHiaNeOeS.

Calculated,%: C 41.09; H 4.14; N 25.87; S 7.31.

Example 7

1- (2-nitrobenzenesulfonide) -3- [4-dimethylamino-6- (a-methyl) propylideneiminooxy-1,3,5-triazin-2-yl] urea (compound 6).

Analogously to that described in Example 2, 2-nitrobenzenesulfonyl isocyanate and 2-amino-4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazine give the above-mentioned urea with a melting point of 187-189 ° C .; the yield is 85%.

Found; %: C 41.92; H 4.39; N 24.16; S 7.11. CieHaoNsOeS.

Calculated,%: C 42.48; H 4.46; N 24.77; S 7.08.

Example 8

1- (2-nitrobenzenesulfonyl) -2- (4-dimethylamino-6-benzylideniminooxy-1,3,5-triazin-2-yl) urea (compound 7).

Analogously to that described in Example 2, 2-nitrobenzenesulfonyl isocyanate and 2-amino-4-dimethylamino-6-benzylideneiminooxi-1,3,5-triazine give the above-mentioned urea with a melting point of 194-196 ° C. in 82% yield.

Found,%: C 46.73; H 3.69; N 23.02; S 6.61; CisHisNsOeS.

Calculated,%: C 46.91; H 3.73; N 23.03; S 6.59.

Example 9

1- (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideneiminooxy-1,3,5-triazin-2-yl) urea (compound 8).

Analogously to that described in Example 2, 2-methoxycarbonylbenzenesulfonyl isocyanate and 2-amino-4-dimethylamino-6-isopropylideneiminooxy-1,3,5-triazine give the above-mentioned urea with a melting point of 187-189 ° C. in 90% yield .

Found,%: C 45.5; H 5.0; N 21.57; S 7.24; C17H21N7O6S.

Calculated,%: C 45.23; H 4.69; N, 21.72; S 7.10.

Example 10

1- (2-methoxycarbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylideniminooxy-1,3,5-triazin-2-yl] urea (Compound 9).

Analogously to that described in Example 2, 2-methoxycarbonylbenzenesulfonyl isocyanate and 2-amino-4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazine give the above-mentioned urea with a melting point of 170 ° C. (below Decompose). The yield is 92%.

Found,%: C 46.51; H 5.08; N 21.08; S 6.62. C18H23N7O6S.

Calculated,%: C 46.45; H 4.98; N 21.06; S 6.89.

Example 11

1- (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-benzyldeniminooxy-1,3,5-triazin-2-yl) urea (compound 10).

Analogously to that described in Example 2, 2-methoxycarbonylbenzenesulfonyl isocyanate and 2-amino-4-dimethylamino-6-benzylideneiminooxy-1,3,5-triazine give the above-mentioned urea with a melting point of 163-164 ° C. (with decomposition). The yield is 91%.

Found,%: C 50.27; H 4.36; N 19.84; S 6.13. C21H21N7O6S.

Calculated,%: C 50.50; H 4.24; N 19.68; S 6.42.

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Example 12

1- (2-Methoxycarbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (2-chloro) benzylideniminooxi-1,3,5-triazin-2-yl] urea (compound 11).

Analogously to that described in Example 2, 2-methoxycarbonylbenzenesulfonyl isocyanate and 2-amino-4-dimethylamino-6- (2-chloro) benzylideneiminooxi-1,3,5-triazine give the above-mentioned urea with a melting point of 162-163 ° C. (with decomposition). The yield is 96%.

Found,%: C 47.64; H 3.93; N 18.64; CI 6.26; S 5.75. CaiHaoCINyOeS.

Calculated,%: C 47.24; H 3.78; N 18.36; CI 6.64; S 6.0.

Example 13

1- (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxy-1,3,5-triazin-2-yl) urea (compound 12).

Analogously to that described in Example 2, 2,5-dichlorobenzenesulfonyl isocyanate and

2-Amino-4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazine, the above-mentioned urea, melting point 170-172 ° C. in 90% yield.

Found,%: C 38.81; H 3.48; Cl 15.01; N 20.96. C15H17CI2N7O4S.

Calculated,%: C 38.97; H 3.77; Cl 15.96; N, 21.21.

Example 14

1- (2,5-dichlorobenzenesulfonyI) -3- [4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazin-2-yl] urea (compound 13).

Analogously to that described in Example 2, 2,5-dichlorobenzenesulfonyl isocyanate and

2-Amino-4-dimethylamino-6- (a-methyl) propyIideniminooxi-1,3,5-triazine the above-mentioned urea melting point 154-156 ° C in 92% yield.

Found,%: C 40.68; H 4.05; N 20.55; CI 14.54; S 6.15. C16H19CI2N7O4S.

Calculated,%: C 40.34; H 4.02; N 20.59; CI 14.88; S 6.73.

Example 15

1- (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxy-1,3,5-triazin-2-yl) urea (compound 14).

Analogously to that described in Example 2, 2,5-dichlorobenzenesulfonyl isocyanate and

2-Amino-4-dimethylamino-6-benzylideniminooxi-1,3,5-triazine the above-mentioned urea with a melting point of 180-182 ° C in 87% yield.

Found,%: C 44.51; H 3.08; Cl 13.82; N 18.96. C19H17CI2N7O4S.

Calculated,%: C 44.72; H 3.36; Cl 13.89; N 19.22.

Example 16

1- (2,6-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylidiminooxi-1,3,5-triazin-2-yl) urea (compound 15).

Analogously to that described in Example 2, 2,6-dichlorobenzenesulfonyl isocyanate and

2-Amino-4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazine the above-mentioned urea with a melting point of 168-170 ° C in 85% yield.

Found,%: C 40.12; H 3.9; Cl 15.54; N 21.54; C15H17CI2N7O4S.

Calculated,%: C 38.97; H 3.71; Cl 15.34; N, 21.21.

Example 17

1- (2,6-dichlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methy!) Propylideniminooxi-1,3,5-triazin-2-yl] urea (compound 16).

Analogously to that described in Example 2, 2,6-dichlorobenzenesulfonyl isocyanate and

2-Amino-4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazine, the above-mentioned urea, melting point 164-166 ° C. The yield is 86%.

Found,%: C 40.62; H 4.08; CI 15.20; N 20.81; Ci6Hi9CI2N704S.

Calculated,%: C 40.34; H 4.02; Cl 14.88; N 20.59.

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Example 18

1- (2,6-dichlorobenzenesulfonyI) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea (compound 17).

Analogously to that described in Example 2, 2,6-dichlorobenzenesulfonyl isocyanate and

2-Amino-4-dimethylamino-6-benzylideniminooxi-1,3,5-triazine the above-mentioned urea with a melting point of 171-173 ° C in 89% yield.

Found,%: C 44.98; H 3.70; Cl 14.12; N 19.49. C19H17CI2N7O4S.

Calculated,%: C 44.72; H 3.36; Cl 13.83; N 19.22.

The IR and ESR'-H spectra of the substituted phenylsulfonyltriazinylureas are shown in Table 1.

Table 1

IR and ESRLH spectra of the substituted phenylsulfonyltriazinyl ureas

Current No.

Ri

R2

R3

R4

1

2nd

3rd

4th

5

1.

ci h

chs ch3

2nd

cl h

ch3

C2H5

3rd

cl h

h c6h5

4th

cl h

h c6h4ci-2

5.

NO2

h ch3

ch3

6.

NO2

h ch3

C2H5

7.

NO2

h h

c6h5

8th.

CO2CH3

h ch3

ch3

9.

CO2CH3

h ch3

C2H5

10th

CO2CH3

h h

c6h5

11.

CO2CH3

h h

c6h4ci-2

12th

Cl

5-ci ch3

ch3

13.

Cl

5 — Cl ch3

C2H5

14.

Cl

5-ci

H

cËHS

15.

Cl

6-Cl ch3

CHs

16.

CI

6 — Cl

CHs

C2H5

17th

Cl

6-ci

H

CeHs

11

5

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Table 1 (continued)

Current number 1

IR spectrum (KBr) cm-1 vso2 vc = N 6 7

vco 8

ISR spectrum,

8 NH

9

ppm SNH 10

1.

1360

1450

1721

13.59

9.33

1160

1623

2nd

1367

1450

1710

13.62

9.28

1178

1618

3rd

1365

1460

1705

13.82

9.61

1180

1605

4th

1365

1470

1705

13.85

9.66

1178

1605

5.

1365

1455

1712

13.60

10.65

1170

1605

6.

1360

1460

1715

13.66

10.15

1170

1600

7.

1375

1480

1712

13.91

9.85

1180

1610

8th.

1362

1472

1738

13.08

8.75

1173

1614

1704

9.

1363

1465

1726

13.01

8.80

1165

1616

1708

10th

1360

1465

1732

13.90

8.80

1165

1615

1705

11.

1363

1465

1725

13.88

8.92

1165

1610

1708

12th

1370

1460

1703

13.62

9.21

1182

1595

13.

1380

1455

1710

13.65

9.25

1160

1600

14.

1370

1460

1708

13.95

9.91

1175

1605

15.

1368

1450

1705

13.58

9.35

1180

1600

16.

1370

1460

1703

13.61

9.41

1182

1604

17th

1360

1465

1705

13.62

9.72

1180

1610

Example 19

Sodium salt of 1- (2-chlorobenzenesulfony!) - 3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea (compound 18).

A solution of 0.6 g (0.015 mol) of sodium hydroxide in 20 ml of water is added in portions with stirring, 4.28 g (0.01 mol) of 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi- 1,3,5-

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CH 683 341 A5

triazin-2-yl) urea. The reaction mixture is stirred at a temperature between 40 and 45 ° C within 3 hours until the sulfonylurea dissolves. The reaction mixture obtained is filtered off, the water is evaporated under reduced pressure at a temperature of 50.degree. The residue is washed with ether and dried under vacuum. 4.3 g (90%) of the above-mentioned salt of melting point 178 ° C. (with decomposition) are obtained.

Found,%: C 40.21; H 3.96; N 22.0; S 7.36. Ci5Hi7CIN704SNa.

Calculated,%: C 40.04; H 3.78; N 21.8; S 7.12.

Example 20

Sodium salt of 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazin-2-yl] urea (compound 19).

Analogously to that described in Example 19, sodium hydroxide and 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazin-2-yl) urea the salt mentioned above in 92% yield with 161 ° C melting point (with decomposition).

Found,%: C 41.42; H 4.09; Cl 7.66; N 21.14. CieHigCIN / CUSNa.

Calculated,%: C 41.48; H 4.13; Ci 7.59; N, 21.18.

Example 21

Sodium salt of 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzyiideniminooxi-1,3,5-triazin-2-yl) urea (compound 20).

Analogously to that described in Example 19, the above-mentioned salt in is obtained from sodium hydroxide and 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea 93% yield with 156 ° C melting point (with decomposition).

Found,%: C 45.83; H 3.42; Cl 7.13; N 19.69. Ci9Hi7CIN704SNa.

Calculated,%: C 45.91; H 3.48; Cl 7.31; N 19.66.

Example 22

Sodium salt of 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (2-chlorobenzylideniminooxi-1,3,5-triazin-2-yi] urea (compound 21).

Analogously to that described in Example 19, sodium hydroxide and 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (2-chloro / benzylideniminooxi-1,3,5-triazin-2-yl] urea the salt mentioned above, the yield is 95%, the melting point is 158 ° C. (with decomposition).

Found,%: C 42.73; H 3.06; Cl 13.41; N 18.56. CigHieCkNyCUSNa.

Calculated,%: C 42.86; H 3.00; Cl 13.35; N, 18.42.

Example 23

Sodium salt of 1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-y!) Urea (compound 22).

Analogously to that described in Example 19, the above-mentioned salt in is obtained from sodium hydroxide and 1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea 95% yield with a melting point of 184 ° C (with decomposition).

Found,%: C 39.23; H 3.73; N 24.63; S 6.73. Ci5Hi7N806SNa.

Calculated,%: C 39.1; H 3.69; N 24.35; S 6.96.

Example 24

Sodium salt of 1 - (2-nitrobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazin-2-yl] urea (compound 23).

Analogously to that described in Example 19, sodium hydroxide and 1- (2-nitrobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazin-2-yl] urea the above-mentioned salt in 92% yield of melting point 184 ° C (with decomposition).

Found,%: C 40.5; H 4.01; N 23.63; S 6.75. CieHigNsOeSNa.

Calculated,%: C 40.61; H 4.19; N 23.72; S 6.69.

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CH 683 341 A5

Example 25

Sodium salt of 1 - (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea (compound 24).

Analogously to that described in Example 19, the above-mentioned salt in is obtained from sodium hydroxide and 1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea 94% yield from the melting point 185 ° C (with decomposition).

Found,%: C 44.91; H 3.88; N 22.31. CigH ^ NsOeSNa.

Calculated,%: C 44.88; H 3.74; N 22.04.

Example 26

Sodium salt of 1 - (2-methoxycarbonylbenzenesulfonyI) -3- (dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea (compound 25).

Analogously to that described in Example 19, the above-mentioned salt in is obtained from sodium hydroxide and 1- (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea 94% yield from melting point 162 ° C (with decomposition).

Found,%: C 43.12; H 4.23; N, 21.72; S 6.76.

Ci7H2oN706SNa.

Calculated,%: C 43.06; H 4.39; N 21.83;

S 6.82.

Example 27

Sodium salt of 1- (2-methoxycarbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylidene-iminooxy-1,3,5-trlazin-2-yl] urea (compound 26).

Analogously to that described in Example 19, mans obtained from sodium hydroxide and 1- (2-methoxycarbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazin-2-yl] urea the salt mentioned above in 92% yield of 151 ° C melting point (with decomposition).

Found,%: C 44.35; H 4.52; N 20.12; S 6.57. Ci8H22N706SNa.

Calculated,%: C 44.49; H 4.41; N 20.18; S 6.83.

Example 28

Sodium salt of 1 - (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxy-1,3,5-triazin-2-yl) urea (compound 27).

Analogously to that described in Example 19, the above-mentioned salt in is obtained from sodium hydroxide and 1- (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea 93% yield from the melting point 154 ° C (with decomposition).

Found,%: C 48.37; H 3.83; N 18.81; S 6.14. C2iH20N7O6SNa.

Calculated,%: C 48.43; H 3.96; N 18.91; S 6.29.

Example 29

Sodium salt of 1- (2-methoxycarbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (2-chloro / benzylideniminooxy-1,3,5-triazin-2-yl] urea (compound 28).

Analogously to that described in Example 19, urea is obtained from sodium hydroxide and 1- (2-methoxycarbonylbenzenesulfonyl) -3-4-dimethylamino-6- (2-chloro / benzylideniminooxi-1,3,5-triazin-2-yl) the above-mentioned salt in 95% yield from the melting point 157 ° C (with decomposition).

Found,%: C 45.36; H 3.42; Cl 6.39; N 17.64. C2iHi9CIN706SNa.

Calculated,%: C 45.53; H 3.48; Cl 6.44; N 17.59.

Example 30

Sodium salt of 1 - (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea (compound 29).

Analogously to that described in Example 19, sodium hydroxide and 1- (2,5-dichlorobenzensulfonyl) -3- (4-dimethylamino-6-isopropylideneiminooxi-1,3,5-triazin-2-yl) urea give the above-mentioned Salt in 91% yield from the melting point 165 ° C (with decomposition).

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CH 683 341 A5

Found,%: C 37.19; H 3.3; Cl 14.67; N 20.25. Ci5Hi6CI2N704SNa.

Calculated,%: C 37.41; H 3.29; Cl 14.36; N 20.43.

Example 31

Sodium salt of 1 - (2,5-dichlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazin-2-yl] urea (compound 30).

Analogously to that described in Example 19, sodium hydroxide and 1- (2,5-dichlorobenzensulfonyl) -3- [dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazin-2-yl] urea the salt mentioned above in 92% yield with a melting point of 151 ° C.

Found,%: C 38.55; H 3.61; Cl 14.26; N 19.68. Ci6Hi8CI2N704SNa.

Calculated,%: C 38.41; H 3.79; Cl 14.31; N 19.74.

Example 32

Sodium salt of 1- (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea (compound 31).

Analogously to that described in Example 19, sodium hydroxide and 1 - (2,5-dichlorobenzensulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea give the above-mentioned Salt in 93% yield from the melting point 174 ° C (with decomposition).

Found,%: C 42.86; H 3.01; Cl 13.35; N, 18.42. Ci9Hi6Cl2N704SNa.

Calculated,%: C 42.71; H 3.31; Cl 13.21; N 18.31.

Example 33

Sodium salt of 1 - (2,6-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea (compound 32).

Analogously to that described in Example 19, the above-mentioned is obtained from sodium hydroxide and 1- (2,6-dichlorobenzensulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea Salt in 92% yield from melting point 157 ° C (with decomposition).

Found,%: C 37.19; H 3.3; Cl 14.67; N 20.24. Ci9Hi8CI2N704SNa.

Calculated,%: C 37.48; H 3.49; Cl 14.53; N 20.44.

Example 34

Sodium salt of 1- (2,6-dichlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazin-2-yl] urea (compound 33).

Analogously to that described in Example 19, sodium hydroxide and 1- (2,6-dichlorobenzensulfonyl) -3- [4-dimethyiamino-6- (a-methyl / propylideniminooxi-1,3,5-triazine-2- yl] urea the above salt in 92% yield from the melting point 160 ° C (with decomposition).

Found,%: C 38.55; H 3.61; Cl 14.25; N 19.68. Ci6Hi8CI2N704SNa.

Calculated,%: C 38.63; H 3.76; Cl 14.59; N 19.67.

Example 35

Sodium salt of 1- (2,6-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea (compound 34).

Analogously to that described in Example 19, the above-mentioned is obtained from sodium hydroxide and 1- (2,6-dichlorobenzensulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea Salt in 92% yield from the melting point 167 ° C (with decomposition).

Found,%: C 42.86; H 3.01; Cl 13.35; N, 18.42. Ci9Hi6CI2N704SNa.

Calculated,%: C 42.93; H 3.13; Cl 13.49; N 18.91.

Example 36

Potassium salt of 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-y!) Urea (compound 35).

A solution of 0.84 g (0.015 mol) of potassium hydroxide in 25 ml of water is added in portions with stirring 4.28 g (0.01 mol) of 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi- 1,3,5-triazin-2-yl) urea. The reaction mixture is mixed at a temperature between 40 and 45 ° C15

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CH 683 341 A5

the temperature within 3 hours until the sulfonylurea dissolves. The reaction mass obtained is filtered off, the water is evaporated under reduced pressure at a temperature of at most 50 ° C. The residue is washed with ether, dried under vacuum and 4.5 (90%) of the above salt with a melting point of 181 ° C. is obtained.

Found,%: C 38.81; H 3.63; N 20.97; S 6.98. C15H17CIN7O4SK.

Calculated,%: C 38.67; H 3.65; N 21.05; S 6.87.

Example 37

Potassium salt of 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxy-1,3,5-triazin-2-yl] urea (Compound 36).

Analogously to that described in Example 36, from potassium hydroxide and 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazin-2-yl] urea the above-mentioned salt in 92% yield from the melting point 163 ° C (with decomposition).

Found,%: C 40.15; H 3.90; Cl 7.19; N 20.51. C16H19CIN7O4SK.

Calculated,%: C 40.04; H 3.96; Cl 7.4; N 20.43.

Example 38

Potassium salt of 1 - (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea (compound 37).

Analogously to that described in Example 36, the above-mentioned salt in is obtained from potassium hydroxide and 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea 94% yield from the melting point 169 ° C (with decomposition).

Found,%: C 44.59; H 3.43; Cl 6.72; N 18.95. C19H17CIN7O4SK.

Calculated,%: C 44.4; H 3.31; Cl 6.91; N 19.08.

Example 39

Potassium salt of 1 - (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (2-chloro / benzylideniminooxi-1,3,5-triazin-2-yl] urea (Compound 38).

Analogously to that described in Example 36, urea is obtained from potassium hydroxide and 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6 (2-chloro) benzylideniminooxi-1,3,5-triazin-2-yl] the above-mentioned salt in 91% yield from the melting point 164 ° C (with decomposition).

Found,%: C 41.74; H 2.85; Cl 12.82; N 17.70. C19H16CI2N7O4SK.

Calculated,%: C 41.6; H 2.92; Cl 12.96; N 17.88.

Example 40

Potassium salt of 1 - (2-nitrobenzenesu! Fonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea (compound 39).

Analogously to that described in Example 36, potassium hydroxide and 1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-isopropy! Ideniminooxi-1,3,5-triazin-2-yl) urea give the above Salt in 93% yield with a melting point of 186 ° C. (with decomposition).

Found,%: C 37.69; H 3.49; N 23.68; S 6.59. CisH ^ NsOeSK.

Calculated,%: C 37.82; H 3.57; N 23.53; S 6.72.

Example 41

Potassium salt of 1 - (2-nitrobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazin-2-yl] urea (compound 40).

Analogously to that described in Example 36, from potassium hydroxide and 1- (2-nitrobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazin-2-yl] urea the above salt in 95% yield from the melting point 189 ° C (with decomposition).

Found,%: C 39.35; H 3.76; N 22.72; S 6.70. CisHigNsOeSK.

Calculated,%: C 39.18; H 3.88; N 22.86; S 6.53.

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CH 683 341 A5

Example 42

Potassium salt of 1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea (compound 41).

Analogously to that described in Example 36, the above-mentioned salt in is obtained from potassium hydroxide and 1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea 91% yield with 187 ° C melting point (with decomposition).

Found,%: C 43.65; H 3.71; N 21.25; S 6.06. CigH ^ NsOeSK.

Calculated,%: C 43.51; H 3.62; N 21.37; S 6.11.

Example 43

Potassium salt of 1 - (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideneiminooxy-1,3,5-triazin-2-yl) urea (compound 42).

Analogously to that described in Example 36, the above-mentioned salt in is obtained from potassium hydroxide and 1- (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideneiminooxi-1,3,5-triazin-2-yl) urea 92% yield from the melting point 168 ° C (with decomposition).

Found,%: C 41.58; H 4.02; N 20.34; S 6.68. Ci7H2oN706SK.

Calculated,%: C 41.71; H 4.08; N 20.16; S 6.54.

Example 44

Potassium salt of 1- (2-methoxycarbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxy-1,3,5-triazin-2-yl] urea (Compound 43).

Analogously to that described in Example 36, potassium hydroxide and 1- (2-methoxycarbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazin-2-yl] urea the salt mentioned above in 93% yield with 153 ° C melting point (with decomposition).

Found,%: C 42.71; H 4.42; N 19.61; S 6.22. CisHaaNyOeSK.

Calculated,%: C 42.9; H 4.37; N 19.48; S 6.36.

Example 45

Potassium salt of 1- (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxy-1,3,5-triazin-2-yl) urea (compound 44).

Analogously to that described in Example 36, the above-mentioned salt in is obtained from potassium hydroxide and 1- (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea 95% yield with 159 ° C melting point (with decomposition).

Found,%: C 46.84; H 3.65; N 18.09; S 5.81. C21H20N7O6SK.

Calculated,%: C 46.93; H 3.72; N, 18.25. S 5.96.

Example 46

Potassium salt of 1- (2-methoxycarbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (2-chloro / benzylideniminooxy-1,3,5-triazin-2-yl] urea (Compound 45).

Analogously to that described in Example 36, potassium hydroxide and 1- (2-methoxycarbenylbenzenesulfonyl) -3- [4-dimethylamino-6- (2-chloro / benzylideniminooxi-1,3,5-triazin-2-yl] urea the above-mentioned salt in 92% yield from the melting point 166 ° C (with decomposition).

Found,%: C 44.22; H 3.43; Cl 6.15; N, 17.02. C21H19CIN7O6SK.

Calculated,%: C 44.09; H 3.32; Cl 6.21; N, 17.44.

Example 47

Potassium salt of 1 - (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea (compound 46).

Analogously to that described in Example 36, potassium hydroxide and 1- (2,5-dichlorobenzensulfonyl) -3- (4-dimethylamino-6- (isopropylidiminooxi-1,3,5-triazin-2-yl) urea give this the above-mentioned salt in 94% yield with a melting point of 168 ° C. (with decomposition).

Found,%: C 35.87; H 3.27; Cl 14.32; N 19.44. C15H16CI2N7O4SK.

Calculated,%: C 36.00; H 3.2; Cl 14.2; N 19.6.

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CH 683 341 A5

Example 48

Potassium salt of 1 - (2,5-dichlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazin-2-yl] urea (compound 47).

Analogously to that described in Example 36, potassium hydroxide and 1- (2,5-dichlorobenzensulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazine-2- yl] urea the above salt in 93% yield with 153 ° C melting point (with decomposition).

Found%: C 37.29; H 3.43; Cl 13.90; N 19.21. C16H18CI2N7O4SK.

Calculated,%: C 37.35; H 3.5; Cl 13.81; N 19.06.

Example 49

Potassium salt of 1 - (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea (compound 48).

Analogously to that described in Example 36, potassium hydroxide and 1- (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea give the above-mentioned Salt in 95% yield with a melting point of 178 ° C. (with decomposition).

Found,%: C 41.69; H 2.95; Cl 12.81; N 17.76. CigHìeClaNyCUSK.

Calculated,%: C 41.6; H 2.92; Cl 12.95; N 17.88.

Example 50

Potassium salt of 1 - (2,6-dichlorobenzenesulfonyI) -3- (4-dimethylamino-6-isopropylidiminooxi-1,3,5-triazin-2-yl) urea (compound 49).

Analogously to that described in Example 36, the above is obtained from potassium hydroxide and 1- (2,6-dichlorobenzensulfonyl) -3- (4-dimethylamino-6-isopropylideneiminooxi-1,3,5-triazin-2-yl) urea Salt in 96% yield with a melting point of 163 ° C. (with decomposition).

Found,%: C 35.91; H 3.12; Cl 14.08; N 19.78. C15H18CI2N7O4SK.

Calculated,%: C 36.00; H 3.2; Cl 14.2; N 19.6.

Example 51

Potassium salt of 1- (2,6-dichlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propyleneiminooxi-1,3,5-triazin-2-yl] urea (compound 50).

Analogously to that described in Example 36, potassium hydroxide and 1- (2,6-dichlorobenzensulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazine-2- yl] urea in 95% yield with 162 ° C melting point (with decomposition).

Found,%: C 37.50; H 3.61; Cl 13.74; N, 18.99. Ci6Hi8Cl2N704SK.

Calculated,%: C 37.35; H 3.5; Cl 13.81; N 19.07.

Example 52

Potassium salt of 1- (2,6-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea (compound 51).

Analogously to that described in Example 36, potassium hydroxide and 1- (2,6-dichlorobenzensulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea give the above-mentioned Salt in 91% yield with 169 ° C melting point (with decomposition).

Found,%: C 41.52; H 2.88; Cl 12.76; N 17.71. C19H16CI2N7O4SK.

Calculated,%: C 41.6; H 2.92; Cl 12.95; N 17.88.

Example 53

Diethyl ethanol ammonium salt of 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea (compound 52).

A solution of 1.8 g (0.015 mol) of diethylethanolamine in 20 ml of water is added in portions with stirring 4.3 g (0.1 mol) of 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi- 1,3,5-triazin-2yl) urea. The reaction mixture is mixed at a temperature between 40 and 45 ° C within 3 hours until the sulfonylurea is dissolved. The reaction mass obtained is filtered off, the water is evaporated at the reduced pressure at a temperature of at most 50 ° C. The oily residue is washed twice with ether from that

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CH 683 341 A5

Excess diethylethanolamine, dried under vacuum to a constant weight at room temperature and 5.4 g (100%) of the above salt.

Found,%: C 46.48; H 5.97; N 20.87; CI 6.92. C21H33CIN8O5S.

Calculated,%: C 46.28; H 5.87; N 20.57; CI 6.52.

Example 54

Diethyl ethanol ammonium salt of 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylidene-iminooxi-1,3,5-triazin-2-yl] urea (compound 53).

Analogously to that described in Example 53, diethylethanolamine and 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-2-yl] urea give this the salt mentioned above, which is an oily residue in 92% yield.

Found,%: C 47.45; H 6.60; Cl 6.70; N 20.38; S 6.01. C22H35CIN8O5S.

Calculated,%: C 47.21; H 6.27; Cl 6.36; N 20.01; S 5.73.

Example 55

Diethyl ethanol ammonium salt of 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea (compound 54).

Analogously to that described in Example 53, the above-mentioned salt is obtained from diethylethanolamine and 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea, which is an oily residue in 94.5% yield.

Found,%: C 50.39; H 5.18; Cl 6.31; N 18.54; C25H33CIN8O5S.

Calculated,%: C 50.72; H 5.58; Cl 6.00; N 18.93.

Example 56

Diethyl ethanol ammonium salt of 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (2-chloro / benzylidene-iminooxi-1,3,5-triazin-2-yl] urea (compound 55).

Analogously to that described in Example 53, diethylethanolamine and 1- (2-chlorobenzenesulfonyl) -2- [4-dimethy! Amino-6- (2-chloro / benzylideniminooxi-1,3,5-triazine-2- yl] urea is the salt mentioned above, which is an oily residue in 96% yield.

Found,%: C 47.50; H 5.58; CI 11.65; N 18.03. C25H32CI2N8O5S.

Calculated,%: C 47.85; H 5.10; Cl 11.32; N 17.86.

Example 57

Diethyl ethanol ammonium salt of 1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxy-1,3,5-triazin-2-yl) urea (compound 56).

Analogously to that described in Example 53, the above-mentioned salt is obtained from diethylethanolamine and 1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea, which is an oily residue in 94% yield.

Found,%: C 45.79; H 5.80; N 22.31; S 5.48. C2iH33N907S.

Calculated,%: C 45.40; H 5.94; N 22.70; S 5.76.

Example 58

Diethyl ethanol ammonium salt of 1- (2-nitrobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylidene-iminooxi-1,3,5-triazin-2-yl] urea (compound 57).

Analogously to that described in Example 53, diethylethanolamine and 1- (2-nitrobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazin-2-yl] urea is the salt mentioned above, which is an oily residue in 98% yield.

Found,%: C 46.11; H 6.50; N 22.51; S 5.90. C22H35N9O7S.

Calculated,%: C 46.40; H 6.15; N 22.14; S 5.62.

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CH 683 341 A5

Example 59

Diethyl ethanol ammonium salt of 1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea (compound 58).

Analogously to that described in Example 53, the above-mentioned salt is obtained from diethylethanolamine and 1- (2-nitrobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea, which is an oily residue in 96% yield.

Found, %. C 50.02; H 5.91; H 21.32; S 5.75. CasHseNaOyS.

Calculated,%: C 49.75; H 5.47; IM 20.90; S 5.31.

Example 60

Diethyl ethanol ammonium salt of 1- (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethyiamino-6-isopropyl-ideniminooxi-1,3,5-triazin-2-yl) urea (compound 59).

Analogously to that described in Example 53, the above-mentioned salt is obtained from diethylethanolamine and 1- (2-methoxy-carbonylbenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea , which is an oily residue in a yield of 92%.

Found,%: 48.21; H 6.72; N 20.01; S 6.10. CasHaeNsO / S.

Calculated,%: C 48.59; H 6.31; N 19.72; S 5.63.

Example 61

Diethyl ethanol ammonium salt of 1- (2-methoxycarbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazin-2-yl] urea (compound 60).

Analogously to that described in Example 53, diethylethanolamine and 1- (2-methoxy-carbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl) propylideniminooxi-1,3,5-triazin-2-yl] are obtained from urea is the salt mentioned above, which is an oily residue in a yield of 94%.

Found,%: C 49.12; H 6.14; N 18.95. C24H38N8O7S.

Calculated,%: C 52.60; H 5.84; N 18.18.

Example 62

Diethyl ethanol ammonium salt of 1- (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-benzylidene-iminooxi-1,3,5-triazin-2-yl) urea (compound 61).

Analogously to that described in Example 53, the above-mentioned salt is obtained from diethylethanolamine and 1- (2-methoxycarbonylbenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-trlazin-2-yl) urea, which is an oily residue in a yield of 94.5%.

Found,%: C 52.93; H 6.20; N 18.50. C21H21N7O6S.

Calculated,%: C 52.60; H 5.84; N 18.18.

Example 63

Diethyl ethanol ammonium salt of 1- (2-methoxycarbonylbenzenesulfonyl) -3- [4-dimethylamino-6 (2-chloro / benzylideniminooxi-1,3,5-triazin-2-yl] urea (compound 62).

Analogously to that described in Example 53, diethylethanolamine and 1- (2-methoxy-carbonylbenzenesulfonyl) -3- [4-dimethylamino-6- (2-chloro / -benzzyiideniminooxi-1,3,5-triazin-2-yl ] urea is the salt mentioned above, which is an oily residue in a yield of 93%.

Found,%: C 49.59; H 5.01; Cl 5.06; N 16.92. C21H20CIN7O6S.

Calculated,%: C 49.81; H 5.38; Cl 5.46; N, 17.22.

Example 64

Diethyl ethanol ammonium salt of 1- (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylidene-iminooxi-1,3,5-triazin-2-yl) urea (compound 63).

Analogously to that described in Example 53, diethylethanolamine and 1- (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideneiminooxy-1,3,5-triazin-2-yl) urea give the above-mentioned Salt, which is an oily residue in a yield of 92%.

Found,%: C 43.94; H 5.98; Cl 12.60; N 19.70. C21H32CI2N8O5S.

Calculated,%: C 43.52; H 5.53; Cl 12.26; N 19.34.

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CH 683 341 A5

Example 65

Diethyl ethanol ammonium salt of 1- (2,5-dichlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propyl-ideniminooxi-1,3,5-triazin-2-yl] urea (compound 64).

Analogously to that described in Example 53, diethylethanolamine and 1- (2,5-dichlorobenzenesulfonyl) -3- [4-dimethylamino-6-) a-methyl / propylideniminooxi-1,3,5-triazine-2- yl] urea is the salt mentioned above, which is an oily residue in a yield of 92.5%.

Found,%: C 44.89; H 6.02; C 12.34; N 19.21. C22H34CI2N8O5S.

Calculated,%: C 44.52; H 5.73; Cl 11.97; N 18.89.

Example 66

Diethyl ethanol ammonium salt of 1- (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylidenimino-oxi-1,3,5-triazin-2-yl) urea (compound 65).

Analogously to that described in Example 53, diethylethanolamine and 1- (2,5-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea give the above Salt, which is an oily residue in a yield of 95%.

Found,%: C 48.03; H 5.48; Cl 11.60; N, 18.11. C25H32CI2N8O5S.

Calculated,%: C 47.85; H 5.10; Cl 11.32; N 17.86.

Example 67

Diethyl ethanol ammonium salt of 1- (2,6-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylidenimino-oxi-1,3,5-triazin-2-yl) urea (compound 66).

Analogously to that described in Example 53, diethylethanolamine and 1- (2,6-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylideniminooxi-1,3,5-triazin-2-yl) urea give the above-mentioned Salt, which is an oily residue in a yield of 97.5%.

Found,%: C 43.14; H 5.19; Cl 11.85; N 19.01. C21H32CI2N8O5S.

Calculated,%: C 43.52; H 5.53; Cl 12.26; N 19.34.

Example 68

Diethyl ethanol ammonium salt of 1- (2,6-dichlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propyl-ideniminooxi-1,3,5-triazin-2-yl] urea (compound 67).

Analogously to that described in Example 53, diethylethanolamine and 1- (2,6-dichlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazine-2- yl] urea is the salt mentioned above, which is an oily residue in a yield of 96.5%.

Found,%: C 44.19; H 5.31; Cl 11.51; N 18.59. C22H34CI2N805S.

Calculated,%: C 44.52; H 5.73; Cl 11.97; N 18.89.

Example 69

Diethyl ethanol ammonium salt of 1- (2,6-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylidenimino-oxi-1,3,5-triazin-2-yl) urea (compound 68).

Analogously to that described in Example 53, diethylethanolamine and 1 - (2,6-dichlorobenzenesulfonyl) -3- (4-dimethylamino-6-benzylideniminooxi-1,3,5-triazin-2-yl) urea give the above-mentioned Salt, which is an oily residue in 98% yield.

Found,%: C 47.49; H 4.85; Cl 10.93; N 17.50. C25H32Cl2N805S.

Calculated,%: C 47.85; H 5.10; Cl 11.50. N 17.86.

Example 70

The biological activity of the claimed compounds was estimated. For this purpose, the influence of the representatives of these compounds, the 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-iso-propylideniminooxi-1,3,5-triazin-2-yl) urea (compound 1) and 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / propylideniminooxi-1,3,5-triazin-2-yl] urea (Compound 2), on growth and development The maize and cucumber seedlings were examined and, under laboratory conditions, the plants were grown on the soil in vessels weighing 0.5 kg, filled with a mixture of soil: sand: peat (3: 1: 1).

When fertilizing before germination, the substances were removed by Be21 immediately after sowing the seeds

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CH 683 341 A5

spraying the surface of the soil entered. When the preparations were fertilized after germination, the plants were sprayed into the dicotyledon phase. In each vessel, 10 ml of a 0.00062% aqueous solution, based on the active ingredient, was introduced, which corresponds to a consumption standard of 20 g / ha.

Gibberellin and atrazine were used as etalon.

The biological activity according to the stem growth, the amount of the above-ground raw mass, the development speed and after the growth of the young leaves compared to the control (without soil treatment) was assessed in 3-4 weeks after the treatment.

The number of repetitions according to the variants is 4 times. The test results are shown in Tables 2-4 in percent for control.

Table 2

Influence of compound 1 on the growth of the maize stem in a dose of 20 g / ha acquisition time / day from the moment of germination / 6 8 10 13 15 17 21 height of the stem in% for control 135 * 144 * 125 * 123 * 123 "117 * 109

Table 3

Influence of compound 1 on the growth rate of young maize plants at a dose of 20 g / ha

Acquisition time (day from the moment of germination)

Length of the sheets of the upper material in% for checking

Width of the sheets of the upper material (middle of the sheet) in% for checking

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125

128x

28

153x

178x

38

173

202x x = detectable deviation from the control at P = 0.95

Table 4

Influence of compounds 1 and 2 on the amount of above-ground mass of maize and cucumber seedlings, determined after 3 weeks from the time of germination (the results are given in percent for the untreated control).

Dose of the substance, g / ha

1000

1000

50

20th

Culture

Corn

Connection 1

-

114

116

142

Culture

cucumber

Connection 1

116

162x

104

-

Connection 2

123

132x

130x

-

x = detectable deviation from the control at P = 0.95

As can be seen from the data given in Tables 2 and 3, compound 1 at a dose of 20 g / ha stimulates the growth of the maize stalk at the earlier stages of development of the young maize plants; As a result, the dimensions of the leaf blades of the bracts at the time of the floor measurement are significantly larger than in the control. According to the information given in Table 4, the acceleration of the development of the maize and cucumber seedlings leads to the fact that the above-ground biomass of the plants, grown on the soil treated with compounds 1 and 2, significantly exceeds the biomass of the control plants.

Example 71

The biological activity of the substituted phenylsulfonyltriazinylureas was estimated as a function of their influence on the growth of the maize and cucumber seedlings. The procedure is analogous to Example 70. The acceleration characteristic number of the seedlings is the weight of the above-ground mass of the three-week-old seedlings compared to the control (above-ground mass of the seedlings, grown on the untreated soil). The comparison of the biological activity with that after

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Structure-related compounds which have a herbicidal and growth-regulating activity, the following formula

N (CHv) o R JL 5 2

ir N

k.k so2nhcohh ocHj where R is CI (compound A), R is CO2CH3 (compound B) and with the herbicide, Glin (chlorosulforon as active ingredient)

CH,

A

[ÂN ^

SO2nhcohh- ^ N> ^ 0CH?

and with a known growth stimulant for plants, gibberellin and herbicide, and a growth stimulant for maize, atrazine, (6-isopropylamino-2-chloro-4-ethylamino-1,3,5-triazine).

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CH 683 341 A5

The results are shown in Table 5.

Table 5

Influence of substituted phenylsulfonyltriazinylureas on the growth of maize and cucumber seedlings

connection

Corn

cucumber

Dose of the substance in g / ha

100

20th

100

20th

1

116

142x

162

102

2nd

136x

130x

132x

125

3rd

128x

103

96

143

4th

97

104

151x

109

5

106

114

98

147x

6

92

136x

131x

111

7

131x

123

115

98

8th

100

109

95

139x

9

136x

127x

102

146x

10th

105

121

108

155x

11

148x

95

92

140x

12th

121

154x

113

88

13

98

97

136x

116

14

90

141x

123

120

15

118

102

120

148

16

89

135x

98

109

17th

127x

125

146x

122

Compound A

47x

83

64x

90

Compound B

31x

60x

20 "

53x

Glean

0X

6X

0X

8X

Gibberellin

91

101

86

95

Atrazine, dose 1 kg / ha

123x 0.5 kg / ha 114

-

-

x = detectable deviation from the control at P = 0.95

It can be seen from the information given in Table 5 that the claimed compounds cause a demonstrable stimulation of the growth of the above-ground mass of maize and cucumber, while compounds A, B and Glin are characterized by growth stagnation or a retardation effect.

Gibberellin calls for a stem extension and has no positive influence on the biomass of the aerial part of the plant; as a result, they became thin and falling.

Atrazine acted analogously to the claimed compounds, but the doses were 10 to 25 times higher.

Example 72

The influence of compounds 52 and 53 on the growth and development of the common weeds was examined. The methodology of performing the experiment is similar to that described above. The influence of the preparations on the growth and development of the weeds was estimated based on the weight of the biomass of the aerial plant part in 3 weeks after sowing. The agent in the form of an aqueous glycol solution was added to the soil before sowing the seeds. The results are shown in Table 6 in percent for the control (without treatment of the soil).

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Table 6

Influence of compounds 52 and 53 on weed growth

Type of weeds

Dose of the substance in g / ha

Connection 52

Connection 53

100

20th

100

20th

white goose foot

88

97

81

105

shaggy fox tail

93

102

106

107

Chicken millet

75x

89

79

90

Bristle millet

82

107

94

100

odorless chamomile

96

103

106

97

* = Verifiable deviation from the control at P

= 0.95

From the information given it can be seen that the compounds 52 and 53 have an insignificant influence on the growth and development of the weeds at the earlier stages of organogenesis, that is to say to selectively stimulate several crop plants, their position being more advantageous in the competition.

Example 73

The influence of the claimed compounds 52 and 53 on the weedability and the harvesting of maize was assessed in the field trial. The compounds mentioned were used in the form of aqueous glycol solutions for fertilization before germination in doses of 20 and 50 g / ha, based on the active ingredient. The area of the plots to be considered is 70 m2, the number of repetitions of treatment is 4 times. The area of the plot is dark gray, padded, slightly loamy, the humus content is 1.5%, the pH is 4.0. The weed species on the test plot are preferably as follows: odorless chamomile, shepherd's purse, water pepper, chickweed, field horsetail, common grasshopper. The following results were achieved.

In 1985, the green crop when using the compounds 52 in a dose of 20 g / ha was 149%, based on the control, and in a dose of 50 g / ha 176%, the weed infestation was 98% at the two doses reduced. The same result was achieved in 1986. Weedability was reduced by 85% at a dose of 20 g / ha and by 72% at a dose of 60 g / ha. The harvest of the sour feed mass was 136%, based on the control (at a dose of 50 g / ha.) The action of these compounds led to the inhibition to the same extent both of annual dicotyledonous weeds and of weeds. The use of compound 53 in a dose of 20 g / ha increased the yield of the green crop of maize to 173 dt / ha and in a dose of 40 g / ha to 86 dt / ha. The total harvest was 120 dt / ha (MED (minimum essential difference) 0.5 = 82 dt / ha).

It is obvious that the use of glucose, which is highly toxic to maize, and compounds A and B, which inhibit maize growth, are unsuitable in the field (Table 5).

Example 74

The influence of compound 53 on weed infestation and the harvest of wheat and barley was investigated in a field trial.

Compound 53 in the form of an aqueous glycol solution was used in the fertilization before germination in doses of 10 and 20 g / ha, based on the active ingredient. The area of the plots to be considered is 36 m2, the number of repetitions of treatment is 4 times. The bottom of the plot is a typical Chernozem, a strongly loamy soil with a humus content of 4.5% (pH = 7.0) , Fox tail, shepherd's purse, Ak-winch, field horsetail, goose thistle.

The following results were achieved. In a dose of 10 g / ha, compound 53 caused the death of 45% of the weeds in winter wheat sowing, the yield increase being 8.4 dt / ha. Glinetalon is 2.1 dt / ha. (The crop in the control is 25 dt / ha, HCPo, 5-4.0 dt / ha.) Compound 53 in the barley seed caused 42% and 58% of the weeds to die in doses of 10 g / ha and 20 g / ha. The increase in yield amounts to 0.5 or 5.2 dt / ha. The glinetalon (10 g / ha) is equal to 2.9 dt / ha (the harvest in the control is 25.3 dt / ha, MEDo.s 2.0 dt / ha).

Similar results were obtained when the biological activity of the sodium and potassium salts of the substituted phenylsulfonyltriazinylureas was examined.

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Example 75

The influence of the stressed compounds on the cotton harvest was examined - compounds 2, 9, 10, 11, 14.

Apply to the cotton plants in the phase of flower formation by spraying means in the form of an aqueous emulsion with a surfactant, taken in an amount of 0.1% by mass, with the working fluid consumption standard of 500 l / ha. The area of the plot to be considered is 3 m2, the number of repetitions of treatment is 3 times. The cotton variety is Tashkent-1.

The results obtained are shown in Table 7.

Table 7

Comparative evaluation of agents containing substituted ureas of general formula

Connections, No.

medium

R2

Ri

R3

R4

2nd

h cl

CHs

C2H5

9

H

CO2CH3

ch3

C2H5

10th

H

CO2CH3

H

CeHs

11

H

CO2CH3

h c6h4ci-2

14

Cl cl h

c6h5

control

Table 7 (continued)

Connection, no.

Dose, g / ha 10

50

100

dt / ha for control,%

dt / ha for control,%

dt / ha for control,%

2nd

39.4

142.9

38.9

140.8

33.5

121.3

9

33.8

122.6

31.4

113.4

34.7

125.9

10th

28.1

101.7

26.6

96.4

34.6

125.3

11

45.6

165.2

40.6

147.2

34.8

126.2

14

36.3

131.4

20.3

106.0

32.2

116.8

control

27.6

Note: MEDo, i = 9.6 dt / ha

Commercial usability

The claimed compounds, substituted phenylsulfonyltriazine ureas and salts thereof are active ingredients of the agent according to the invention for stimulating and suppressing plant growth which is used in agriculture.

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Claims (4)

Claims 1. Substituted phenylsulfonyltriazinylureas and their salts of general formula: NCCHJJ ,. n n SO 2NHC0M J ^ 0 -N = CR3 wherein R1 for Cl, N02, COOCHa R2 for H, CI R3 for H, CH3 R4 stands for CHs, C2H5, CeHs, C6H4CI-2 and X is absent or c2H5 / X for K, Na, hh - cghe \ C2H4qh stands. 2. Means for stimulating and suppressing plant growth, which provides an active ingredient and a thinner, characterized in that it contains substituted phenylsulfonyltriazinyl-ureas or their salts as claimed in claim 1. 3. Means for stimulating and suppressing plant growth according to claim 2, characterized in that it is 1- (2-chlorobenzenesulfonyl) -3- (4-dimethylamino-6-isopropylidenimino-oxi-1,3,5-triazine-2) as active ingredient -yl) urea or its potassium, sodium or diethyl ethanol ammonium salt of general formula: a ci SOgNHCONH H (CH3) 2 , CH. \ CH. wherein X is missing or / c "h-2? XfürK, Na, HN — CjHc \ c2h4oh is included. 4. Means for stimulating and suppressing plant growth according to claim 2, characterized in that it is 1- (2-chlorobenzenesulfonyl) -3- [4-dimethylamino-6- (a-methyl / pro-pylideniminooxi-1,3) as active ingredient 5-triazin-2-yl] urea or its potassium, sodium or diethyl ethanol ammonium salt of the following formula: 27 5 10th 15 20th 25th 30th 35 40 45 50 55 CH 683 341 A5 j-CCHj) ri 'Q-N = / CH3 .. x SO.NHCOKH ° -N = c ^ 'C H 2 5 wherein X is missing or ° 2h5 X for K, Na, NH— ^ 2 ^ 5 ^ C2H ^ oh stands, contains. 28