WO1991013880A1 - Substituted penylsulphonyltriazinylurea and salts thereof and means for stimulating and suppressing plant growth based on them - Google Patents

Abstract

Substituted phenylsulphonyltriazinylurea and salts thereof have general formula (I), where R1 is Cl, NO¿2?, COOCH3; R?2¿ is H, Cl; R3 is H, CH¿3; R?4 is CH¿3?, C2H5, C6H5, C6H4Cl-2 and X is not present or X is K, Na, α. The claimed means for stimulating and suppressing plant growth contains as an active substance the substituted phenylsulphonyltriazinylurea, or salts thereof of the above-mentioned formula.

Description

ZΑΜΞSCHΕΗΗYΕ ΦSCHSHSHΟSHL gShZShShShΟChShSh, IΧ SΟLI And SΡΕDSΤΒΟ DΙYA SΤIΙSHIΡΟΒΑΗSH and PΟDSHΕΗIΕ ^"ΡΟSΤΑ ΡΑSΤΞΗY ΗΑ IΧ ΟSΗΟΒΕ Οblasτ τeχniκi 5 Ηasτοyaschee izοbρeτenie οτnοsiτsya κ ορganichesκοy χi- mission and τοchnee κ nοvym sοedineniyam - substituted φenil- sulφοnilτρiazinilmοcheviny, iχ sοlyam and sρedsτvu for sτi- muliροvaniya and inhibition of plant growth on their basis.

The predominant level of technology is 10. An important issue in the agricultural sector is the extension of the crop. For this purpose, we use stimulating substances and herbicides.

The simultaneous use of the residents and the stimulation of the growth cause a lot of difficulties, since the 15 specificity of the agriculture depends on the species.

Various compounds known for their active activity are known. For example, the Ι- / 2-chloro-benzene sulfonyl-3- / 4-methyl-6-methoxy-Ι, 3,5-20-thiazin-2-yl / urea compound is known. The product is used on the basis of the aforementioned connection in the agricultural sector to protect the crops of wheat, barley, wheat, wheat and flax, so that there is only 4 crops.

Substances are also known, possessing, for all of them, 25 cidal activity activity of the plant growth regulator. As a matter of fact, the effect of these substances is compatible with the resultant, stable or formative effects. These compounds are derived from general aromatic sulfate urea of the general formula

where Ε = σι, СΟСΗο, σн - 2 -

Such compounds in the dose of 60-400 g / ha exhibit damaging properties and possess a standard, stable or formative effect (P5, Α, 4231784). However, well-known compounds inhibit the growth of cultivated plants.

DISCLOSURE OF THE INVENTION The claimed compounds are new and have not been described in the literature. The basic task of the invention is to create new compounds having a stimulating activity with a simultaneous herbicidal effect.

The problem is solved in that new compounds are proposed which are substituted by phenylsulfonyl and iazinyl urea and their general formula

where Ε ¹ = σι, ΝΟ ₉ , σοοσн,

Ε ² = n, σι

χ - οτсуτсτвуеτ или

χ - missing or

° 5 /

2 = Κ, 1Τa, ШΤ - σ ^ σ ^ οн

The claimed compounds possess a stimulating and active activity. - 3

Means for the stimulation and suppression of the growth of supplies, containing the active substance and the diluent, as agreed on the supply of the power supply and the other are connected. The claimed invention is, according to the invention, preferably contains с- / 2-benzene-sulfide-dimethyl-amine-3- / 4-amine-active material.

10-Ι, 3,5-β-thiazin-2-yl / -urea or its potassium, sodium or diethyl ethanolamine salt of the following formula:

где χ - οτсуτсτвуеτ или σ₂н₅

where χ is absent or σ ₂ n ₅

X = Κ, Νа, ΗΛ σ ₂ n ₅ s ₂ n ₄ on

The claimed invention, according to the invention, may also be predominantly contained in the material, Ι- / 2-coolant-benzyl /--- --2- thiazine-2-yl / urea or its potassium, sodium or diethyl ethanolamine salt of the following formula:

where - are missing or - 4 -

σ ₂ n ₅

X = Κ, Νа, Ηϊ ^' σ ₂ % σ ₂ н ₄ он

The claimed funds possess high activity and are used to stimulate and inhibit the growth of plants. 5 Better embodiment of the invention Declared new compounds - substituted phenyl-sulphonylureas urea - are substances which are highly resistant to white matter.

Declared substituted phenylsulfonyl-iazinyl-urea, the interaction of substituted benzene-sulfonyl isocyanates with substituted 2-amine-Ι, 3,5-β-chazines

Ε ¹ = cι, ΝΟ ₂ , σοοσн ₃ ;

Ε "Η, 01;

σ^σι-2,

σ ^ σι-2,

15 Original components are free at a weight ratio of 1: 1. The process is sold to an organic consumer (benzene, acid, carbohydrate, acetylated, tetrahydride) in - 5 -

In case of catalytic amounts of methyl ester diamine at a temperature of 50-60 ° 0 for 2 hours.

Then, the temperature of the reaction mass is reduced to 20 ° 0 5 and the mixture is stirred for another 2 hours before the complete completion of the reaction. The plant is filtered, washed with a distributor, and the reaction and dried.

The claimed compounds may also be obtained by the reaction of a substituted arylsulfonamide with a diluted 10-nylisocyanate and a substituted 2-amine, 3,5-thiazole in a 60

Ε ¹ = cι, ΝΟ ₂ , σοοσн ₃ ; Ε ² = n, σι Ε ³ = n, σn ₃ ;

Ε ^ = 0Η ₃ , - ^ ₂ ^ _{5 '} ^ ₆ % _' s ^ n ^ σι-2.

The synthesized substituted phenylsulfonate urea synthesis processes were proven by elemental analysis methods, G- and π-spectroscopy. The spectra were recorded on the “ΡΙΕ т ι ι ι ι ι""" ”panel in the ΚΒ p. ΜΡπе τ ΜΡ ΜΡ - 6 -

Taken on the "ta -250" unit in the operation with the use of a thermocamethylsilane as a part of the internal standard. Аче As an example, PΜΡ-sectect Ι- / 2-lορ-

5 benzene sulfonyl / -3- / 4-dimethylamine-6-isopropylphenylidene-oxy - Ι, 3,5-thiazin-2-yl / urine; /, 6Η dimethylamine group and 3.11 ppm / d /, 6Η signals of the phenyl ring are observed

S 7.5-7.7 ppm / m /, ЗΗ and 8.22 ppm / dΗ, Signals of two groups are observed at 9.33 ppm / s / ΙΗ and 13.59 Μ. D. / C / ΙΗ. The assignment of the indicated signals was proved to be unambiguous with the use of synthesized urea sulfide labeled with nitrogen at the same time.

15 sulphamide groups. Sπin sπinοvοe ^{ρasscheπlenie-1} ^ -n signal πρi 13.59 ppm , Equivalent to 90 Hz, made it possible to unambiguously remove this resonant signal to the input of the sulfide group.

Salts of Substituted Phenylsulfonyltiazinyl Urea

20 It is a matter of distress to industrial materials that are consumable in water and inorganic substances, for example, in the presence of glycine.

The claimed salts result in the interaction of substituted phenylsulfonyl ureasinyl ureas with alkali hydroxide.

25 ng ^' metal (each or na- tury) or diethylamine laminate with a mass ratio of 1: 1.1, in the range of the consumer (alcohol) or in the range of 40. The structure of the claimed salt is proved by the methods of ПΜΡ and И-spectroscopy. Like in PΜΡspekt

30 Νa - the salts of Ι- / 2-chloro-benzene sulfonyl / -3- / 4-dimethylamine--6-isopropylpilidenimine-oxy-1,3,5-τ-thiazin-2-yl / urea, which are removed, do not disrupt the signal. For the interactions of the claimed substituted ureas with fatty amines, oily compounds are used.

35 times. Elemental analysis, for example, for the product of the interaction of diethylethanolamine and the aforementioned substituted urea, indicates an addition of 1 between the reactants. - 7 -

Β ShνGΡ sπeκτρe eτοgο adduκτa, snyaτοm in deyτeροatseτοne, οτsuτsτvuyuτ ^signals' προτοnοv οbοiχ amidnyχ προτοnοv, chτο svideτelsτvueτ οb οbρazοvanii sοedineniya, imeyusche- gο sοleοbρazny χaρaκτeρ.

Below is the data of YAG £ Ρ - the compounds of the declared memorized substituted urea and its sodium and diethyl ethanolamine salt:

7.69-8. ΙZsh, Αg

10.69s Ν Ή:

2

Ι3.5Ιs ΝΗ

7.58-8.03m, Αg

9.13s, ΝΗ 8 -

(с ₂ н ₅ ) ₂ κσн ₂ sn ₂ он 2.98ς, СΗ ^ С ^)

Z.Ι5th, Ν (СΗ ₃ ) ₂

3.8m, СΗ ₂ СΗ ₂

6.35s, 0Η

7.5-δ.Ιm Αg

I) Sites I have taken on the “ha -250” unit with a frequency of ⁺ 250.13 MHz.

The information provided here is based on the following case for 5 declared salt:

All of the claimed compounds have a stimulating and inhibiting growth activity. - 9 -

The claimed compounds are active substances for stimulating and inhibiting the growth of plants. The effectiveness of the claimed compounds and devices

5 basics has been studied on plants in laboratory and left-handed conditions.

The claimed compounds have the property of substantially accelerating the growth of cultural plants in the process of phangiogenesis, which leads to phytogenesis.

10 more large plant growths, that is, there are declared connections of selective crops that stimulate only large-scale cultivation, simultaneous growth and growth.

Biological tests of the declared compounds on grains, (for example, wheat, barley), have been carried out

15 bulk and loose and revealed that the reported compounds for herbicidal and stimulating activity of natural clay and gib.

Gibberin, causing lengthening of the stem, did not show

20 positive impact on the biomass of the terrestrial part of the plant, as a result of their growth, they were exhausted, resting. The product operates in a similar manner to the claimed compound, but at a cost of 10 and 25 times.

All compounds claimed are minor substances

25 sts, w> s ₀ on white mice, internally muscle content> 5000 mg / kg. Medium based on declared substances may be used in the form of wettable powders, granules and disinfectants. The inventive device is intended for the treatment of green plants, soil and soil, methods

30 sprinkling, sprinkling, soaking or draining the seeds.

For better understanding of the present invention, the following communication methods for the claimed compounds, testing and activity and application are given.

35 Example I.

Ι- / 2-hydrobenzene sulfonamide - - / 4-dimethylamine-6-isopropylideneimino-oxi-3, 5-τ-thiazin-2-yl / urea / compound I /. - 10 -

Suspensions of 9.57 g / 0.05 mol / 2-chloro-benzensulfonamide and 0.3 ml of methyl tetylethylenediamine in 100 ml of hydroxyethylamine add 7.1 g / 0.05 mol / ml of sulfate 20 ° C. The inactive mixture is heated for 3 hours at a temperature of 95 -00 ° C, cooled and added 11.2 g / 0.05 mol / 2-amino-4-dimethylamine-6-isopropyl-di-iminazinase; the mixture is heated for 3 hours at a temperature of 50-60 ° C, it is cooled, the precipitate is filtered, it is 10 yt and it is produced 17.0 g / 80 / of compound I, mp. 184-186 ° C / from acetone /.

Found,% \ C 41.94; Η 4.34; W 22.81;

C16.96; 5 8.14; C _Ι5 Η _Ι8 C1 Ν _? 0 ₄ . Calculated,%: C 42.11; Η 4.24; 15 Ν 22.92; 018.28; 5 7.50.

For example, 2.

Ι- / 2-hydrochlorobenzene sulfonyl / -3- / 4-dimethylamine-6-iso-προπilidenimine-oxy-Ι, 3,5-τρiazin-2-yl / urea (compound I). 20 Κ suspensions 19.0 g / 0.09 mol / 2-amino-4-dimethyl-amino-6-isopropyl-imidin-oxy-Ι, 3,5-thiazine in 50 ml of benzene, heated to a temperature of 60 ° С, is available A solution of 21.7 g / 0.1 mol / 2-chlorobenzene sulfonylisocyanate in 100 ml of benzene. The effective weight of 25 is stirred for 3 hours at a temperature of 60-70 ° C, and then 2 hours at a room temperature. Additives are pre-washed, washed with benzene, dried and obtained 36.5 g / 95 $ / Ι- / 2-chlorobenzene sulfenyl / -3- / 4-dimethylamine-6- -isopropyl-imidene-imidene-2-imidene / urea, 30 T..pl. Ι84-Ι86 ° C. The data of the elemental analysis are identical to those given in Example I. Example.

I-C2-Alobenzene sulfonyl Z-3-4-dimethylamine-6- (- with methyl) προπilidenimino-oxi-1,3,5-τρiazin-2-yl] mo- 35 chevina (compound 2).

Κ Suspensions 2.06 g Сθ, 0092 mol) 2-amine-4-dimethylamino-6- / Y-methyl / propylidene imine-oxi-3,5-thiazine in 40 ml of dry benzene add I am in the process - II -

lendiamine, the mixture is heated to a temperature of 50-60 ° C and add 2.15 g / 0.0099 mol / 2-chlorobenzene sulfonylation. The active mixture is stirred for 2 hours at a temperature of 5 ° at 60 ° C and 2 hours at a temperature of 20 ° C, the precipitate is filtered and supplied with 4.0 g / 95 $ / s. 172-173 ° C (with ρpl.).

Found,: C 43.22; Η 4.68; Ν 22.31;

C17.81; 37.46; C _χb Η ₂₀ C1 Ν _? 0 ₄ .

10 Calculated, $: C 43.49, Η 4.56, 22.19,

C18.02, 37.25. Example 4.

Ι- / 2-Alobenzene sulfonyl / -3- / 4-dimethylamine-6- -benzylidene imino-oxy-Ι, 3,5-τρiazin-2-yl / urea 15 (compound 3).

Analogous example I of 2-chlorobenzene sulfonylisocyanate and 2-carboxylic acid-4-dimethylamine-6-benzylideneimine oxy--1,3,5-τ-thiazine produces the above-mentioned urea, τ. πl. Ι78 ° С, output is quantitative. 20 Found, $: C 47.67; Η 4.05; Ν 20.65;

Calculated, $: C 47.95; Η 3.81; Ν 20.65;

C1 7.45; 56.73. EXAMPLE 5. 25 Ι- / 2-Alobenzene sulfonyl / -3-4-dimethylamino-6- - (2-colo) -benzylidene imino-oxi-1,3,5-τρiazin-2-yl] manoquine (compound 4).

Similarly, 2 of 2-benzene sulfonylamine and 2-amino-4-dimethylamine-6- / 2-acid / benzylidene-30 n-oxi-Ι, 3,5-βazine are better than the previous one. Ι67-Ι68 ° С, yield 96.5.

Found, $: C 44.80; Η 3.64; Ν 18.94;

01 13, 76; 3 6, 34; σ _{Ι 9} Η _Ι7 Cϊ ^ _? 0 ₄ 3.

Calculated: C 44.71; Η 3, 36; Ν 19.22; 35 C1 13.89; 3 6, 28. - 12 -

Example 6.

Ι- / 2-Vitaminobenzene sulfonyl / -3- / 4-dimethylamine-6- -isopropylphenyleneimine-oxi-Ι, 3,5-τρiazin-2-yl / urea 5 (compound 5).

Analogous example 2 of 2-nitrous benzene sulfonyl-cyanide and 2-amino-4-dimethylamine-6-isopropylphenidenimine-oxy-Ι, 3,5-β-thiazine, the abovementioned. Ι90-Ι92 ° С, yield 88 $. 10 Found, $: C 40.87; Η 4.21; Ν 25.35;

Calculated, $: 041.09; Η 4.14; Ν 25.87;

57.31. EXAMPLE 7. 15 Ι- / 2-Hydro-benzene sulfonide-3- [4-dimethylamine-

-6- (-methyl) προπilidenimine oxy-Ι, 3,5-τρiazin-2-yl] urea (compound 6).

Similarly, 2 of 2 nitrous benzene sulfonylisocyanate and 2-amino-4-dimethylamine-6- (ο <-methyl) πp-20-pylydenimine-oxy, I have been improved. Ι87-Ι89 ° σ, yield $ 85.

Found, $: C 41.92; Η 4.39; Ν 24.16; 57.11.

Calculated, $: 042.48; Η 4.46; Ν 24.77; 25 37.08.

Example 8.

I-C2-Vitamin benzene} -3-4-dimethylamine-6-benzylidenimine oxi-1,3,5-τ-thiazin-2-yl) urea (compound 7). 30 In a similar fashion, 2 of 2 nitrous benzene sulfonyl sulfate and 2-amino-4-dimethylamine-6-benzisdenimine oxy-1, 3,5-τ-thiazine produce the above-mentioned urea τ.pl. Ι94-Ι96 ° σ, yield 82 $.

Found: C 46.73; Η 3.69; Ν 23.02;

Calculated, $: 046.91; Η 3.73; Ν 23.03; s 6.59. - thirteen -

Example 9.

I-2-Methoxycarbonylbenzene sulfonyl) -3- (4-dimethylamine-6-isopropylphenideniminoxy-5, 3,5-thiazin-2-yl) - 5-chevine (compound 8).

Similarly, 2 of 2-methoxybenylbenzene-sulfonylisocyanate and 2-amino-4-dimethylamino-6-isopropo-pylydenimino-oxi-i have been excluded. Ι87-Ι89 ° σ, exit 90. 10 Found, $: 045.5; Η 5.0; Ν 21.57; 3 7.24.

^С Ι7 ^Η 2Ι ^Ν 7 ° 6 ^{3 *} Calculated, $: С 45,23; Η 4.69; Ν 21.72, 37.10.

Example 10.

I- C2-Methoxylated benzene sulfonyl) -3- [4-dimethyl-

15 amino-6- (ο <-methyl) προπilidenimine oxy-Ι, 3, 5-τρiazin-2-

-yl] urea (compound 9).

For a similar example, 2 of 2 methanesobenzene-phenylisocyanate and 2-amine-4-dimethylamine-6- (ο <-methyl) προ- π-polymethine-substituted are 3.5-times

20 urea, τ. πl. Ι70 ° С /ρзл. /. Βыχοд 92 $.

Found, $: C 46.51; Η 5, 08; Ν 21, 08;

Calculated, 046.45; Η 4.98; Ν 21.06; 56.89. . Example II. 25 Ι- / 2-Methoxybenylbenzene sulfonyl / -3- / 4-dimethylamino-6-benzylideniminoxy-1,3,5-τraziazin-2-yl / urea / (compound 10).

In a similar fashion, 2 of 2 methanesobenzene-phenylisocyanate and 2-amino-4-dimethylamine-6-benzylidene-30 nioxy-Ι, 3,5-τ-thiazine are the aforementioned. πl. Ι63-Ι64 ° σ / ρl./, Βыχοд 91 $.

Found, $: 050.27; Η 4.36; q 19.84; 56.13.

^C 2Ι ^Η 2Ι ^Ν 7 ° 6 ³ '

Calculated, $: C 50.50; Η 4.24; Ν 19.68; 35 3 6.42. - 14 -

Example 12.

Ι- / 2-Methoxycarbonylbenzene sulfonyl / -3- [4-dimethylamino-6- (2-chloro) benzylidene imino-oxi-3,5-τraziazin-2-yl] 5 urea (compound II).

Similarly, 2 of 2-methoxybenzene-phenylizanate and 2-amino-4-dimethylamino-6- / 2-hydroxy-benzylidenimino-oxy-azinazinazinazinazinazinazinazinazinazinazino Ι62-Ι63 ° σ /ρpl./. 96ыχοд 96 $. Yu Fide, $: C 47.64; Η 3.93; Ν 18.64;

Calculated, $: C 47.24; Η 3.78; Ν 18.36; 016.64; 3 6.0. 15 Example 13.

Ι- / 2,5-Dichlorobenzenesulfonyl / -3- C4-dimethylamine- -6-isopropylphenylidene imino-oxi-1,3,5-τρiazin-2-yl) urea (compound 12).

A similar example of 2 of 2,5-dichlorobenzene sulfo- 20 nilizocyanate and 2-amine-4-dimethylamino-6-isopropoupilidene-imino-oxi-1,3,5-thiazine results in the aforementioned. Ι70-Ι72 ° σ. 90ыχοд 90 $.

Found, $: 038.81; Η 3.48; σ 15.01;

Ν 20.96. σ _Ι5 n _Ι7 σι ₂ Ν ₇ ο ₄ s.

25 Calculated, $: 038.97; Η 3.77; Ν 15.96;

321.21. Example 14.

I-C2,5-Dichlorobenzene sulfonyl) -3- [4-dimethylamine- -6- (methyl) προπilideniminoox-1,3,5-τiazin-2-yl] мo-30 chevine (compound 13).

. - 15 -Similarly, 2 of 2,5-dichlorobenzene sulfonyl anisylate and 2-amine-4-dimethylamine-6-C-methyl) are more potent than 3,5-thiazine. Ι54-Ι56 ° σ. Βыχοд 92 $. 35 Found, $: C 40.68; Η 4.05; Ν20.55; σ 14.54; 36.15.

. - fifteen -

Calculated, $: C 40.34; Η 4.02; Ν 20.59;

C1 14.88; 6.73. Example 15. 5 Ι- / 2,5-Dichlorobenzene sulfonyl / -3- / 4-dimethylamino-6- -benzylidenenimine oxy-Ι, 3,5-τρiazin-2-yl / urea (compound 14).

Analogous to example 2 of 2,5-dichlorobenzene sulfonate isocyanate and 2-amine-4-dimethylamine-6-benzylideneimine-10 oxy-Ι, 3,5-β-thiazine produces the above-mentioned urea τ. Ι80-Ι82 ° С. Luke 87.

Found, $: C 44.51; Η 3.08; Cϊ 13.82; 18.96. σ _{Ι 9} n _Ι7 σι ^^ Ο ^ 3.

Calculated, $: C 44.72; Η 3.36; 0113.89; 15 Ν 19.22.

Example 16.

Ι- / 2, 6-Dichlorobenzene sulfonyl / -3- / 4-dimethylamine- -6-isopropylphenyleneimine-3, 5-τ-thiazin-2-yl / urea (compound 15). 20 Analogous example 2 of 2,6-dichlorobenzene-sulfonate-lower and 2-amine-4-dimethylamino-6-isopropoupylidene-imino-oxi-3,5, 3,5-thiazine, the above is mentioned. Ι68-Ι70 ° σ. 85ыχοд 85 $.

Found, $: 0 40.12; Η 3.9; 0.15.54; 21, 54.

25 ^С ЬЬ Ι7 ^С1 ^ ° 4 ^Β '

Calculated, C 38.97; - Η 3.71; 01 15.34;

Ν 21.21. Example 17.

Ι- / 2 6-Dichloro-benzene sulfonyl / -3- [4-dimethylamine-6- 30 - (s. Methyl) προπilidenimino-oxi-1, 3, 5-τρiazin-2-yl] malein (compound 16).

Similarly, 2 of 2,6-dichlorobenzene sulfonate and 2-amine-4-dimethylamine-6 / omethyl / methylpropylidene-3,5, is better than 3,5. Ι64-Ι66 ° С. 86ыχοд 86 $. 16 -

Found, $: C 40.62; Η 4.08; Cϊ 15.20;

Ν 20.81. σ _{Ι 6} n _Ι9 σι ₂ Ν ₇ ο ₄ s.

Calculated, $: C 40.34; Η 4.02; 0114.88; 5 Ν 20.59.

Example 18.

I- (2,6-dichloro-benzene sulphonyl) -3-C4-dimethylamine- -6-benzylidenenimine oxy-Ι, 3,5-τρiazin-2-yl) urea (compound 17). 10 Analogous example 2 of 2,6-dichlorobenzensulfonyl phenylisocyanate and 2-amino-4-dimethylamino-6-benzyl-denimine oxy-Ι, 3,5-τ-thiazine produce the above-mentioned urea τ. Ι7Ι-Ι73 ° 0. 89ыχοд 89 $.

Ηaπdenο, $: C 44.98; Η 3.70; Cϊ 14.12; 15 Ν 19.49. C _Ι9 Η _Ι7 σϊ ₂ Ν ₇ 0 ₄ 3.

Calculated, $: C 44.72; Η 3.36; 0113.83;

Ν 19.22. F- and PΜΡ-spectra of substituted phenylsulfonyl-τpiazinyl ureas are given in Table I.

Table I

IΚ- and PΜΡ-spectra of substituted phenylsulpho-nyltropyazinyl ureas

ππ Ε Ε ^< Ε- Ε '

I 2 3 4 5

I. σι n sn ₃ σn ₃

3. σι н н ^С 6 ^Η 5

4. σι н н σ _« н - 17 -

Offer Table I

5. ΝΟ, n σn ₃ σn ₃ 6. ΝΟ, n σn ₃ ^C 2 ^Η 5

7. ΝΟ, n n ^C 6 ^Η 5

8. σο ₂ σн ₃ н σн ₃ σн ₃

9. сο ₂ sn ₃ n σн ₃ ^С 2 ^Η 5 ju. σο ₂ σн ₃ н н ^С 6 ^Η 5 ιι. σο ₂ σн ₃ н н σ ₆ н ₄ σе-2

17. σι 6-СΙ Η С ₆ Η ₅

- 19 -

Table I

1 6 7 8 9 10

12.1370 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

17.1360 1465 1705 13.62 9.72

P80 1610

Example 19.

Methyl salt of Ι- / 2-hydroxybenzene sulfonyl / -3- / 4-dimethylamine-6-isopropylphenidenimine oxy-Ι, 3,5-ρ thiazin-2-yl / 5 urea (compound 18).

With a solution of 0.6 g (0.015 mol) of sodium hydroxide in 20 ml of water and stirring, add 4.28 g (0.01 mol) of Ι- / 2-chloro-benzyl-imide-dimethyl-amide Ι, 3,5-τρiazin-2-yl / urea. 10 The active mixture is stirred at a temperature of 40-45 ° 0 for 3 hours before the dissolution of sulfonylurea. The obtained reactive mass is filtered, it evaporates at low pressure and at a temperature not exceeding 50 ° 0. The garden is washed, dried in a vacuum and obtained 15 4.3 g ($ 90) of the above salt, T.pl. Ι78 ° σ /ρl./. - 20 -

Found, $: 0 40.21; Η 3, 96; Ν 22, 0; 3 7.36. С _Ι5 Η _Ι7 Сϊ ₇ 0 ₄ 8Ыа.

Calculated, $: C 40.04; Η 3.78; Ν 21.8.3 7.12. 5 Example 20.

Methyl salt of Ι- / 2-hydrochlorobenzene sulfonyl / -3- / 4-dimethylamine-6- (s-methyl) shrupilidenimin oxy-1,3,5-τ-thiazin-2-yl] urea (compound 19).

Example 19 from sodium hydroxide and Ι- / 2-10 - ^χ lobenzene sulphonyl / -3- / 4-dimethylamine-6-methyl) προπ-lidenimine oxy-2, 3,5-τ iliazin-2 a salted salt with an output of $ 92 T..pl. Ι6Ι ° С /ρзл. /.

Found, $: C 41.42; Η 4.09; σ 7.66; Ν 21.14;

^With Ι6 ^Η Ι9 ^NL 7 ° ^ZΝa 4 ^* 15 Βychislenο, $: C, 41.48; Η 4.13; 01 7.59; Ν 21.18.

Example 21.

Methyl salt of Ι- / 2-chlorobenzene sulfonyl / -3- / 4-dimethylamino-6-benzylidenimine oxy-Ι, 3,5-τρiazin-2-yl / urea (compound 20). 20 similar to example 19 from hydrous oxide and

Ι- / 2-hydroxybenzene sulfonyl / -3- / 4-dimethylamine-6-benzylideneimino-oxy-Ι, 3,5-τρiazin-2-yl / urea produces the above salt with a yield of $ 93 ° C. 56 ° C. /ρzl./. -Found, $: C 45.83; Η 3.42; 017.13;

Calculated, $: C 45.91; Η 3, 48; 01 7.31;

Ν 19.66. Example 22.

Methyl salt of Ι- / 2-hydroxybenzene sulfonyl / -3-4-dime- 30 tylamino-6- / 2-hydroxybenzylidene imine oxy-Ι, 3,5-τρiazin-2-yl] urea (compound 21).

A similar example of 19 from sodium hydroxide and Ι- / 2-chlorobenzene sulfonyl / -3- [4-dimethylamine-6- / 2-chloro-enzylidenimine oxyzene, 3,5-trisylazin 2] . Χыχοд 95 $, τ.pl. Ι59 ° 0 /ρazl. /. Found, $: 042.73; Η 3.06; 0113.41; - 21 -

Ν 18.56. C _Ι9 Η _Ι6 Cϊ _2? 0 ₄ per. ^*

Calculated, $: C 42.86; Η 3.00; C113.35; Ν 18.42. 5 Example 23.

Methyl salt of Ι- / 2-nitrate benzene sulfonyl / -3 - / 4-dimethylamine-6-isopropodiamine-oxi--, 3,5-τ-thiazin-2-yl / urea (compound 22).

Analogous to example 19 from hydropyoxy and 10 Ι- / 2-nitrousbenzene sulfonyl / -3- / 4-dimethylamine-6-iodine-phenyliminin-derived, 3.5-iodine-derived, $ 95, τ.pl Ι84 ° С /ρзл. /. Found, $: C 39.23; Η 3.73; / V 24.63; 56.73. With _Ι5 Η _Ι? Ν ₈ 0 ₆ Per.

15 Calculated, $: C 39.1; Η 3.69; Ν 24.35;

5 6.96. Example 24.

Methyl salt of Ι- / 2-nitrate benzene sulfonyl / -3- (4-dimethyl tylamino-6- / ο <.-Methyl / προπilidenimine oxy-1, 3, 5-trap-20 zin-2-yl] urea (compound )

Analogous to example 19 from sodium hydroxide and Ι- / 2-nitrousbenzene sulfonyl / -3- 4-dimethylamine-6- / ο -methyl / yl-substituted, 3, 5-substituted $ 92, τ.pl Ι84 ° С 25 / ρazl. /.

Found, $: C 40.5; Η 4.01; Ν 23.63; 3 6.75.

^С Ι6 ^Η Ι9 ^Ν 8 ° 6 ^ЗΝа 'Calculated, $: С 40.61; Η 4, Ι9; Ν 23.72; 56.69 30 Example 25.

Methyl salt of Ι- / 2-nitrobenzene sulfonyl / -3- / 4-dimethylamine-6-benzylidenenimine oxy-Ι, 3,5-τ-thiazin-2-yl / urea (compound 24).

Similar to example 19. From sodium hydroxide and 35 Ι- / 2-nitrate benzene sulfonyl / -3- / 4-dimethylamine-6-enzyme-ladenine oxi-Ι, 3,5-τ-thiazine-2-yl / urea is higher than , τ.π. Ι85 ° С /ρзл. /. - 22 -

Found, $: C 44.91; Η 3.88; Ν 22.31. С _Ι9 Η _Ι7 Ν _δ 0 ₆ ЗΝ.

Calculated, $: C 44.88; Η 3.74; Ν 22.04. Example 26.

Methyl salt of Ι- / 2-methoxypropylbenzene sulfonyl / -3 - / - dimethylamine-6-isopropylphenideniminoxy-Ι, 3,5-β-thiazin-2-yl / urea (compound 25).

Analogous to example 19 from sodium hydroxide and Ι- / 2-methoxybenzensulfonyl / -3- / 4-dimethylamino-6-iodine, 3,5-derivatives, 3,5-derivatives , τ.π. Ι62 ° С /ρзл. /.

Found, $: C 43.12; Η 4 * 23; Ν 21.72; 5 6.76. С _Ι7 Η ₂₀ Ν ₇ 0 ₆ ЗΝа.

Calculated, $: C 43.06; Η 4.39; Ν 21.83; 36.82. Example 27.

Methyl salt of Ι- / 2-methoxycarbonyl benzene-phenyl / -3-G4-Dimethylamine-6- / ο-methyl / προπylidenimine-oxy-Ι, 3,5-τρiazin-2-yl) urea (26). Example 19 from sodium hydroxide and Ι- / 2-methoxybenylbenzene sulfonyl / -3- 4-dimethyl-amino-6 -, / ο <. -labeled / προπilidenigline oxy-1,3,5-τρiazin--2-yl] urea receive the above salt, yield $ 92, τ.pl. Ι5Ι ° 0 /ρml./.

Found, $: 044.35; Η 4.52; Ν 20.12;

Calculated, $: 044.49; Η 4.41; Ν 20.18; 5 6.83. Example 28.

Methyl salt of Ι- / 2-methoxycarbonylbenzene sulfonyl / - -3- / 4-dimethylamine-6-benzylidene imine-oxy-Ι, 3,5-β-thiazine-2-yl / urea (compound 27).

Example 19 of sodium hydroxide and Ι- / 2-methoxybenylbenzene sulfonyl / -3- / 4-dimethylamine--6-benzylidenimine oxy-Ι, 3,5-τriazin-2-yl - 23 -

ut the above salt, exiting $ 93, t.pl. Ι54 ° 0 / ρazl, /. Found, $: 048.37; Η 3.83;

Ν 18.81; 3 6.14. C ^ Η ^ Ν ^ 3 a.

5 Calculated, $: C 48.43; Η 3.96;

Ν 18.91; 3 6.29. Example 29.

Methyl salt of Ι- / 2-methoxypropyl benzene sulfonyl / -3- [4-dimethylamine-6- / 2-hydroxy / benzylidene imine oxi-10-3,5, 3,5-τ-thiazin-2-yl] urea (28).

Example 19 from sodium hydroxide and Ι- / 2-methoxypropylbenzene sulphonyl / -3- [4-dimethylamino-6- / 2- ^χ l / ρ-benzylidene-amine-3,5-amine, 2- the above salt, exiting $ 95, τ.pl. 15 Ι57 ° 0 /ρml./.

Found, $: 045.36; Η 3.42; 016.39; Ν 17.64. σ _2Ι Η _Ι9 0ϊΝ ₇ 0 ₆ a.

Calculated, $: C 45.53; Η 3.48; 016.44; Ν 17.59. 20 Example 30.

Methyl salt of Ι- / 2,5-dichloro-benzene sulfonyl / -3- - / 4-dimethylamine-6-isopropylphenidenimine oxy-1,3,5-τ-thiazin-2-yl / urea (compound 29).

Analogous to example 19 from sodium hydroxide and 25 /- / 2,5-dichlorobenzene sulphonyl / -3- / 4-dimethylamine-6-isopropylidenimin-oxy-i exit 91, τ.pl. Ι65 ° 0 /ρazl. /. Found, $: 037.19; Η 3.3; 0114.67; Ν 20.25.

^With Ι5 ^Η Ι6 ^SG 2 4 ° 7 ^{Ν ZΝa} - 30 Βychislenο,: 037.41; Η 3.29; 0114.36;

Ν 20.43. Example 31.

Methyl salt of Ι- / 2,5-dichloro-benzene sulfonyl / -3- 4--dimethylamine-6- / ο-methyl / προπylidenimine-oxi-3, 5-τρ-35 azin-2-yl] urea (compound 30).

Analogous example 19 from sodium hydroxide and I- (2, 5-dichlorobenzene sulfonyl) -3- [4-dimethylamine-6-Сo <-methyl) προπ-depenimine-1, 3, 5-2-azin - 24 -

I receive the above salt, exited $ 92, τ.pl. Ι5Ι ° С /ρзл. /.

Found, $: C 38.55; Η 3.61; 01 14.26; Ν 19.68. C _Ι6 Η _Ι8 Cϊ2 ₇ 0 ₄ 8 a.

Calculated, $: C 38.41; Η 3.79; 01 14.31;

Ν 19.74. Example 32.

Methyl salt of Ι- / 2,5-dichloro-benzene sulphonyl / -3- / 4- -dimethylamine-6-benzene-dehydroxy-1,3,5-τ-thiazin-2-yl / urea (compound 31).

Analogous example 19 from sodium hydroxide and Ι- / 2,5-dichlorobenzene sulphonyl / -3- / 4-dimethylamino-6- is reduced-oxidized, 1,3,5-ρ thiazin-2-yl / urea, , τ.π. Ι74 ° 0 /ρazl. /. Found, $: C 42.86; Η 3.01; 01 13.35;

Calculated, $: C 42.71; Η 3.31; Cϊ 13.21; Ν 18.31. Example 33.

Methyl salt of Ι- / 2,6-dichloro-benzene sulphonyl / -3- - / 4-dimethylamine-6-isopropodiamine-oxi-1,3,5-τ-thiazin-2-id / urea (compound 32).

Analogous example 19 from hydropathy and Ι- / 2,6-dichlorobenzene sulphonyl / -3- / 4-dimethylamine-6- -propylphenidenimin oxy-2, increased-92-yl, τ.pl Ι57 ° С /ρзл. /.

Found, $: C 37.19; Η 3.3; Cϊ 14.67;

Calculated, $: 037.48; Η 3.49: 01 14.53;

Ν 20.44. Example 34.

Methyl salt Ι- (2,6-dichloro-benzene sulphonyl) -3- - [4-dimethylamine-6- (-C-methyl) π ο и и жд жд жд жд жд-1 1 urea (compound 33).

Analogical Example 19 Hydraulics and

Ι- / 2, 6-di ^χ lorebenzene sulfonide / -3- [4-dimethylamine-6- / ο <-methyl / προπilidenimineoco-1, 3, 5-τρiazin-2-urea πο- - 25 -

the above salt is released, exiting $ 92, t.pl. Ι60 ° С /ρзл. /.

Found $: C 38.55; Η 3.61; Cϊ 14.25;

Calculated, $: 038.63; Η 3.76; 0114.59;

Ν 19.67. Example 35.

Methyl salt of Ι- / 2,6-dichloro-benzene sulphonyl / -3-10 - / 4-dl.

For example, 19 of sodium hydroxide and Ι- / 2, 6-dichlorobenzene sulphonyl / -3- / 4-dimethylamine-6-benzene-aminoxi-3, 5-yl was $ 92, τ.pl Ι67 ° С /ρзл. /.

Found, $: C 42.86; Η 3, 01; Cϊ 13.35; Ν 18.42. _Ι9 Η _Ι6 C ^ Ν _? 0 ₄ ЗΝа.

Calculated, $: C 42.93; Η 3.13; C1 13.49; 20 Ν 18.91.

Example 36.

Carbonate salt of Ι- / 2-hydroxybenzene sulfonyl / -3- / 4-methyl-6-isopropylidene, 1, 3, 5-thiazin-2-yl / urea (compound 35). 25 0,8 solution of 0.84 g (0.015 mol) of potassium hydroxide in 25 ml of water and stirring, add 4.28 g (0.01 mol) of Ι- / 2-hydrochlorobenzene / -3-6-di-di isopropylidene-1, 3, 5-τρiazin-2-yl / urea. The active mixture is stirred at a temperature of 30 to 40-45 ° 0 for 3 hours before the dissolution of sulfonylurea. The resulting discharged mass is filtered, they evaporate at low pressure and temperature no higher than 50 ° 0. The garden is washed off, dried in a vacuum and received 4.5 g ($ 90) of the above soot, T.pl. Ι8Ι ° С. 35 Found, $: C 38.81; Η 3.63; Ν 20.97;

3 6.98. C _Ι5 Η _Ι7 σϊΝ ₇ 0 ₄ ЗΕ. - 26 -

Calculated, $: 0 -38.67; Κ 3.65; Ν 21, 05; 3 6.87. EXAMPLE 37. Carbonate salt of Ι- / 2-chlorobenzene sulfonyl / -3- [4-di-methylamine-6- (methyl ester) π ο жд и жд жд жд 1 1 1 с urea (,-di-methyl-2-yl) urea ( 36).

Analogous to example 36 of potassium hydroxide and Ι- / 2-chlorobenzene sulfonyl / -3- [4-dimethylamine-6- ο <methyl) with an output of $ 92, t.pl. Ι63 ° 0 /ρazl. /. Kaiden, $: 0 40.15; Η 3.90; 01 7.19;

Ν 20.51. σ _{Ι 6} n _ιd σϊΝ ₇ ο ₄ wk.

Calculated, $: 0 40, 04; Η 3.96; 01 7.4; 15 Ν 20.43.

Example 38.

Carbonate salt of Ι- / 2-chloro-benzene sulfonyl / -3- / 4-dimethylamine-6-benzylidenenimine-oxy-3, 5-τ iazin-2-yl / urea (compound 37). 20 Analogous example 36 from potassium hydroxide and

Ι- / 2-hydroxybenzene sulfonyl / -3- / 4-dimethylamine-6-benzyl-denimine-oxy-3, 5-τ-thiazin-2-yl / urea produces the above salt with a yield of $ 94. τ.pl Ι69 ° С /ρзл. /. Found, $: C 44.59; Η 3.43; 01 6.72; 25 Ν 18.95. C _Ι9 Η _Ι7 C1Ν ₇ 0 ₄ ЗΚ.

Calculated, $: C 44.4; Η 3.31; Cϊ 6.91;

Ν 19.08. Example 39.

The carbonate salt of /- / 2-chloro-benzene sulfonyl / -3- [4-g-30 methyl-6-G2-colo) benzylidene imine-1, 3, 5-β-thiazin-2-yl] urea (compound 38).

Analogous to example 36 of potassium hydroxide and Ι- / 2-hydrochlorobenzene sulfonyl / -3- [4-dimethylamine-6- (2-carbide) benzylidenimino-1, 3, 5-methylazole] , $ 91, τ.pl. Ι64 ° С /ρзл. /. - 27 -

Found, $: 0 41.74; Η 2.85; 01 12.82;

Calculated, $: C 41.6; Η 2.92; C1 12, 96; 5 Ν 17.88.

Example 40.

Κ- / 2-nitrate benzene sulfonyl / -3- / 4-dimethylamine-6-isopropylidenediamine-3, 5-τ thiazine-2-yl / urea (salt 39). Sizing 36 of the Calcium Hydride and

Ι- / 2-nitrobenzene sulfonyl / -3- / 4-dimethylamino-6-isopropylidene-1, 3, 5-thiazin-2-yl / urea obtained the above salt, the yield was 93, the result was 93, Ι86 ° С /ρзл. /. Found, $: C 37.69; Η 3.49; Ν 23.68; 15 3 6.59. C Η ^ Ο _β 3Κ.

Calculated, $: C 37.82; Η 3, 57, Ν 23.53; 3 6.72.

Example 41.

Евая- / 2-nitrate benzene sulfonyl / -3- [4-yes-20 methylamine-6- (-methyl) π ο и жд жд жд жд ин ин 1 1 1, urea (compound 40).

A similar example of 36 from potassium hydroxide and Ι- / 2-nitrous benzene sulfonyl-3- [4-dimethylamine-6- (b <-methyl) π ο жд ины аз аз]] 2] , $ 95, τ.pl. Ι89 ° С /ρзл. /.

Found, $: C 39.35; Η 3.76; Ν 22.72;

Calculated, $: 0 39.18; Η 3.88; Ν 22.86; 30 3 6.53.

Example 42.

Евая- / 2-nitrate benzene sulfonyl / -3- / 4-dimethylamino-6-benzene-imidine-oxi-3, 5, 5-thiazin-2-yl / male carbide salt (compound 41). 35 The same example 36 from potassium hydroxide and

Ι- / 2-nitro-benzene sulfonyl / -3- / 4-dimethylamine-6-benzene - 28 -

lidenimine oxy-1,3,5-τρiazin-2-yl / urea the above salt is obtained, the yield is 91 $, τ.pl. Ι87 ° 0 /ρazl. /. Found, $: 043.65; Η 3.71; Ν 21.25; 5 3 6.06. C _ιд Η _Ι7 Ν ₈ 0 ₆ ЗΚ.

Calculated, $: C 43.51; Η 3.62; Ν 21.37;

36.11. Example 43.

Each salt of Ι- / 2-methoxybenylbenzene sulfon-10 nil / -3- / 4-dimethylamine-6-of ρ ρ и жд жд жд мин ин ин ин (urea (compound 42).

Analogous to example 36 from potassium hydroxide and Ι- / 2-methoxycarbonylbenzene sulphonyl / -3- / 4-dimethylamine-6-isopropylylidene-oxy-Ι, 3,5-long exit $ 92, τ.pl. Ι68 ° С /ρзл. /. Kaiden, $: C 41.58; Η 4.02; Ν 20.34; h 6.68.

^C Α ^ e ³ '

Calculated, $: C 41.71; Η 4.08; Ν 20.16;

3 6.54. 20 Example 44.

Erasable salt of Ι- / 2-methoxybenylbenzene sulfonyl / -3- 4-dimethylamine-6- (ο-methyl) προπilidenimineoxyl-Ι, 3,5-τρiazin-2-yl urea (compound 43). Αnalοgichnο πρimeρu 36 of gidροοκisi κaliya and 25 Ι- / 2-meτοκsiκaρb οnilbenz ensulφοnil / -3- [4-dimeτilami- nο-6- / ο <-meτil / προπizhdeniminοοκsi-1, 3, 5-τρiazin-2-yl] mο - Chevins receive the aforementioned salt, exited $ 93, τ.pl. Ι53 ° С /ρзл. /.

Found, $: C 42.71; Η 4.42; Ν 19.61; h 6.22. C _Ι8 Η ₂₂ Ν ₇ Ο ₆ ZΚ.

Calculated, $: 042.9; Η 4.37; Ν 19.48;

3 6.36. Example 45.

Carbonate salt of е- / 2-methoxybenzenesulfonyl 35 nyl / -3- / 4-dimethylamine-6-benzylideneimine oxy-1, 3, 5-τρ- - 29 -

azin-2-yl / urea - (compound 44).

Analogous to example 36 from potassium hydroxide and Ι- / 2-methoxycarbonyl benzensulfonyl / -3- / 4-dimethyl-5 amine-6-benzeneziniminooxidine, 3,5-τazin-2-escent outlet 95, τ.pl. Ι59 ° С / ρ

Found, $: C 46.84; Η 3.65; Ν 18.09;

10 Calculated, $: 0 46, 93; Η 3.72; Ν 18.25;

3 5.96. Example 46.

Carbonate salt of м- / 2-methoxybenzenesulfonyl phenyl / -3- [4-dimethylamine-6-G2-hydroxybenzhenimine-15 κ oxy-Ι, 3,5-τρiazin-2-yl] urea (compound 45). Analogous example 36 from potassium hydroxide and Ι- / 2-methoxybenylbenzene benzylphenyl / -3- [4-dimethylamine-6- / 2-xyloup / benzylideneimine oxy-Ι, 3, 5-yl the aforementioned salt, 20 out $ 92, t.pl. Ι66 ° 0 /ρazl. /.

Found, $: C 44.22; Η 3.43; Cϊ 6.15; Ν 17.02. С _2Ι Η _Ι9 С1Ν ₇ 0 ₆ ЗΚ.

Calculated, $: C 44.09; Η 3.32; 01 6.21;

Ν 17.14. 25 Example 47.

Carbonate salt of /- / 2,5-dichloro-benzene sulphonyl / -3- / 4-da-methyl-6-isopropylphenidenimin-oxy-3, 5-τ-thiazin-2-yl / urea (compound 46).

Analogous example 36 of potassium hydroxide and 30 Ι- / 2, 5-dichlorobenzene sulfonyl / -3- / 4-dimethylamine-6- / due to π ο жд жд аз аз ин ин аз аз , exit 94 $, τ.pl. Ι68 ° С /ρзл. /. Found, $: C 35.87; Η 3.27; 01 14.32; Ν 19.44. С _Ι5 Η _Ι6 С1 _{2 7} 0 ₄ ЗΚ.

35 Calculated,: C 36, 00; Η 3, 2; C1 14.2; Ν 19.6. - thirty -

Example 48.

Carbonate salt of χ- (2,5-dichloro-benzene sulphonyl) -3- / 4-methyl-6- (with ^χ . -Methyl ^ προπ-depenimine-oxy-1, 3, 5-τ iazin-5 -2-yl] urea (compound 47 )

Analogous example 36 from potassium hydroxide and Ι- / 2, 5-dichlorobenzene sulphonyl / -3- [4-dimethylamine-6-<methyl) προπilidenimine oxy-Ι, 3, 5-π-i the above salt is released, exiting $ 93, t.pl. Ι53 ° 0 10 /ρpl./.

Found, $: C 37.29; Η 3.43; Cϊ 13, 90; Ν 19.21. С _Ι6 Η _Ι8 Сϊ ^ ₇ 0 ₄ ЗΚ.

Calculated, $: C 37.35; Η 3.5; Cϊ 13.81; Ν 19.06. 15 Example 49.

The carbonate salt of Ι- / 2,5-dichloro-benzene sulfonyl ^ -3- / 4-da-methyl-6-benzene-min-oxy-1, 3, 5-τ-thiazin-2-yl / urea (compound 48).

Analogous to example 36 from potassium hydroxide and 20 Ι- / 2, 5-dichlorobenzene sulfonyl / -3- / 4-dimethylamino-6-benzylzheniminoxoxy-Ι, 3,5-τ iazine-2-yl-amine $ 95, τ.pl Ι78 ° С /ρзл. /. Found:: C 41.69; Η 2, 95; Cϋ 12, 81;

Ν 17.76. C _ιд Η _Ι6 Сϊ ^ ₇ 0 ₄ s.

25 Calculated, $: C 41.6; Η 2.92; 01 12.95;

Ν 17.88. Example 50.

Each salt of Ι- / 2,6-dichloro-benzene sulfonyl / -3- / 4-dimethylamino-6-isopropodiamine-oxy-1, 3, 5-τ iazin-2-yl / mo-30 chevins (compound 49).

Analogous to example 36 from potassium hydroxide and Ι- / 2, 6-dichlorobenzene sulphonyl / -3- / 4-dimethylamine-6-isopropylidene imine-derived, is increased in the case of $ 96, τ.πl _with Ι63 ° 0 /ρazl./. .35 Found, $: C 35.91; Η 3, 12; 01 14.08; - 31 -

Ν 19.78. С _Ι5 Η _Ι8 Сϊ _{2 7} 0 ₄ ЗΚ.

Calculated, $: C 36, 00; Η 3, 2; Cϊ 14.2; Ν 19.6. 5 Example 51.

Carbonate salt of Ι- / 2,6-dichloro-benzene sulfonyl / -3- [4-dimethylamine-6- (s * -methyl) π ο p-de-imidine-oxy-Ι-, 3, 5-ρ thiazin-2-yl] urea (compound 50 )

Αnalοgichnο ^"πρimeρu 36 of gidροοκisi κaliya and 10 Ι- / 2, 6-enz diχlορb ensulφοnil / -3- [4-dime-6- τilaminο / sχ meson τil / προπizhdeniminοοκsi-Ι, 3, 5-τρiazin-2- sludge] urea π - radiates the aforementioned salt, yield $ 95, mp. Ι62 ° С / ρlaz ./.

Found, $: C 37.50; Η 3.61; Cϊ 13.74. 15 Ν 18.89; C _Ι6 Η _Ι8 σι _{2 7} 0 ₄ ЗΚ.

Calculated, $: C 37.35; Η 3.5; Cϊ 13.81;

Ν 19.07. Example 52.

Carbonated salt of Ι- / 2,6-dichloro-benzene sulphonyl / -3- 20 - / 4-dimethylamine-6-benzene-dehydroxy-1,3,5-τρiazin--2-yl / urea (compound 51).

A similar example of 36 from potassium hydroxide and Ι- / 2,6-dichlorobenzene sulfonyl / -3- / 4-dimethylamine-6- -benzene minoxy-1,3,5-τ-thiazin-2-yl / higher is obtained ^. exit 91 $, τ.pl. Ι69 ° С /ρl./.

Found, $: C 41.52; Η 2.88, Cϊ 12.76; Ν 17.71. C _Ι9 Η _Ι6 01 _{2 7} 0 ₄ ЗΚ.

Calculated, $: 041.6; Η 2.92; 0112.95; 30 Ν 17.88.

Pρp 53.

Diethylamine ammonium salt Ι- / 2-chloro-benzensul-phenyl / -3- / 4-dimethylamino-6-isopropylphenidenimin oxy-1,3, 5-thiazin-2-yl / urea (compound 52). 35 g of a solution of 1.8 g (0.015 mol) of diethylamine in 20 ml of water and stirring add - 32 -

4.3 g (0.1 mol) of Ι- / 2-hydrochlorobenzene sulfonyl / -3- / 4-da-methyl-6-isopropylphenidenimine-oxy-3,5-τ-thiazin-2-yl / urea. The reaction mixture is stirred at a temperature of 40-45 ° 0 for 3 hours before the sulfonylurea is dissolved. The resulting reactive mass is removed, which is affected by water pressure and a reduced pressure not exceeding 50 ° С. Desaturated plants 2 times are washed with an excess of diethylethanolamine and dried in a vacuum to reach a reasonable weight of 100 times. Found, $: C 46.48; Η 5.97; Ν 20.87;

Calculated, $: 0 46.28; Η 5, 87; Ν 20.57; Cι 6.52.

Example 54.

Diethylamine ammonium salt Ι- / 2-chloro-benzensul-phenyl / -3- 4-dimethylamino-6- (ο <-methyl) π ο и и жд жд жд 3,5 3,5 3,5 urea (urea). Example 53 of diethylethanolamine and

Ι- / 2-Chlorobenzene sulfonyl / -3- [4-dimethylamine-6- (s-methyl) προπilidenimin oxy-1, 3, 5-thiazin-2-yl] urea is derived from the above, oil and oil are reduced $ 92. Ηa1denο: C 47.45; Η 6.60; Cϊ 6.70;

Ν 20.38; 3 6.01. 0 ₂₂ Η ₃₅ 0ϊ Ν ^ Ο ^ z.

Calculated, $: C 47.21; Η 6.27; C16.36;

Ν 20.01; 3 5.73. EXAMPLE 55. Diethyl ethanolammonium salt Ι- / 2-chlorobenzensulfonyl phenyl / -3- / 4-dimethylamine-6-benzylidene imine oxy-1,3,5-τρ-azin-2-yl / urea (compound 54).

Example 53 of diethylethanolamine and Ι- / 2-chlorobenzene sulfonyl / -3- / 4-dimethylamine-6-benzene-imino-oxy-Ι, 3,5-τ-thiazin-2-yl / urea-urea - 33 -

bathroom salt, which is a self-contained oil plant, with an output of $ 94.5.

Found, $: 0 50.39; Η 5, 18; 01 6.31; 5 Ν 18.54. σ ₂₅ Η ₃₃ 0 ϊ ₈ 0 ₅ 3.

Calculated, $: 0 50.72: Η 5.58; Сϊ 6, 00;

Ν 18.93. Example 56.

Diethylamine ammonium salt Ι- / 2-chloro-benzene sulfon-10 nil / -3-G4-dimethylamino-6- / 2-chloro-benzene-min-oxy-Ι, 3,5-τ-thiazin-2-yl] urea (compound).

Analogous example 53 from diethylethanolamine and Ι- / 2-hydroxybenzene sulfonyl / -2- [4-dimethyl-tylamino-6- (2-carbonyl-benzylidenimine oxy-1, 3, 5-methylazole] , which is a self-contained oil sediment, with an output of $ 96.

Found, $: C 47.50; Η 5.48; C1 11, 65;

^" Calculated, $: 047.85; Η 5.10; C1 11.32; 20 and 17.86.

Example 57.

Diethylammonium salt Ι- / 2-nitrate benzensulphosphate / -3- / 4-dimethylamine-6-iodide-min imoxy-1, 3,5-thiazin-2-yl / urea (compound 56). 25 Example 53 of diethylethanolamine and Ι- / 2-nitrobenzene sulfonyl / -3- / 4-dimethylamine-6-isopropylidene iminoxidine, is more potent, - Lanyi garden, with a yield of $ 94. 30 Found, $: C 45.79; Η 5.80; Ν 22.31; h 5.48. C _2] -Η ₃₃ Ν ₉ 0 ₇ s.

Calculated, $: C 45.40; Η 5.94; Ν 22.70;

3 5.76. EXAMPLE 58. 35 Diethylethanolammonium salt-Ι- / 2-nitrate benzensul- - 34 -

phenyl-3- [4-dimethylamine-6- (<χ-methyl) προπдениминіοκ-si-1, 3, 5-триазин-2-ил] urea (compound 57).

Analogous to 53 diethylethanolamine and 5 /- / 2-nitrous benzene sulfonyl-3- 4-dimethylamine-6- (b <-meashed - flaxen garden, with exit 98.

Found, $: C 46.21; Η 6.50; Ν 22.51;

Calculated, $: C 46.40; Η 6.15; Ν 22.14;

3 5.62. Example 59.

Diethylammonium salt енс- / 2-nitrate benzensul-15 phenyl / -3- / 4-dimethylamine-6-benzene-imine oxy-Ι, 3,5-β-thiazin-2-yl / urea (compound 58).

Similarly, for example, 53 of diethylethanolamine and Ι- / 2-benzyl sulphonyl / -3- / 4-dimethylamine-6-benzyl-isenimoxoxy-1,3,5-thiazine-2-yielded, you get $ 96.

Found, $: C 50.02; Η 5.91; Ν 21.32;

Calculated, $: 049.75; Η 5.47; Ν 20.90; 25 3 5.31.

Example 60.

Э- / 2-Methoxy-diethylammonium salt, benzensulphonyl / -3- / 4-dimethylamine-6-isopropyl-reduced-oxo-Ι, 3,5-τ-thiazin-2-yl / urea (urea). 30 Example 53 of diethanolamine and

Ι- / 2-Methoxybenzenesulfonyl / -3- / 4-dimethylamino-6-isopropodiphenylamine-1,3,5-ρ thiazin-2-yl / urea was added to the aforementioned salt. It’s a special oil garden with a yield of $ 92. 35 Found, $: 048, 21; Η 6.72; Ν 20.01; - 35 -

Calculated, $: C 48.59; Η 6.31; Ν 19.72; 3 5.63. 5 Example 61.

Diethylamine ammonium salt ο- / 2-methoxypropyl-benzensulfonyl / -3- [4-dimethylamine-6-omethyl) π ο π д ени ени 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5]]]]]]]]]]]] 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 3,5 / / э э Similar to example 53 of diethylethanolamine and U 2- / 2-methyl-benzene sulphonyl / -3- [4-dimethylamine-6- - (o salt, which is its own oil seedlings, with an output of $ 94.

Found, $: C 49.12; Η 6.14; Ν 18.95. 15 C ₂₄ Η ₃₈ Ν ₈ 0 _? h.

Calculated, $: C 52.60; Η 5.84; Ν 18.18.

Example 62.

Э- / 2-Methoxy-salt-diethylammonium salt / -3- / 4-dimethylamino-6-benzodzhenimine-20 oxy-Ι, 3,5-τ-thiazin-2-yl / urea (compound).

Analogous example 53 of diethylethanolamine and Ι- / 2-methoxybenyl enensyl sulfonyl / -3- / 4-dimethylamine-6-benzene-reduced-1, 3-5-methylazole , which is a self-contained oil 25th plant, with a yield of $ 94.5.

Found, $: C 52.93; Η 6.20; Ν 18.50.

Calculated, $: C 52.60; Η 5.84; Ν 18.18. Example 63. 30 Diethylammonium salt -Ι- / 2-methoxy-benzene sulfonyl / -3- [ ^~ 4-dimethylamine-6- (2-acid-imine-1, 3, 5-amino) with union 62).

Example 53 of diethylethanolamine and Ι- / 2-methoxylated ensyl ensulfonyl / -3- [4-dimethylamyl-35 nos-6- (2-xylor-benzylidenimine-3-azin-2 ] mο-

- 36 -

Chevins receive the aforementioned salt, which is a special oil plant, with an output of 93.

Found: C 49.59; Η 5, 01; Cϊ 5, 06; 5 Ν 16, 92. С _2Ι Η ₂₀ С1Ν ₇ 0 ₆ 3.

Calculated: C 49.81; Η 5.38; C15.46;

Ν 17.22. Example 64.

Diethylammonium salt Ι- / 2, 5-dichloro-benzene-10 sulfonyl / -3- / 4-dimethyl-amin-6-isopropyl-depenimin-oxy-Ι, 3,5-τ-thiazin-2-yl / urea (compound 63).

Similarly, for example, 53 of diethylethanolamine and Ι- / 2,5-dichlorobenzene sulfonyl / -3- / 4-dimethylamine-6-ispropylidene aminoxidine was used more than 3.5 times Self oil garden, with an output of $ 92.

Found, $: C 43.94; Η 5.98; Cι 12.60; ι 19.70. σ ^ σι ^ s.

Calculated, $: C 43.52; Η 5.53; Cϊ 12.26; 20 Ν 19.34.

Example 65.

Diethylamine ammonium salt Ι- / 2,5-dichloro-benzene-sulfonyl / -3- [4-dimethylamino-6- <χ-methyl π-oxylidene-1,3,5-τ thiazin-2-yl | urea (64) . 25 Example 53 of diethylethanolamine and

Ι- / 2,5-dichloro-benzene sulphonyl / -3- [4-dimethylamine-6- (s-methyl) προπilidenimin oxy-Ι, 3,5-τ-thiazin-2-yl] urea does not cause the above salt, garden, with an output of $ 92.5. 30 Found, $: C 44.89; Η 6.02; 01 12.34; m, 19.21. σ ₂₂ n ₃₄ σι ^ ₈ ο ^.

Calculated, $: C 44.52; Η 5.73; SP 11.97,

Ν 18.89. Example 66. 35 Diethylamine ammonium salt Ι- / 2,5-dichloro-benzene- - 37 -

sulphonyl / -3- / 4-dimethylamine-6-benzene-de-imino-oxy-3, 5-τ-thiazin-2-yl / urea (compound 65).

Αnalοgichnο πρimeρu 53 of dieτileτanοlamina and 5 Ι- /, 5-diχlορbenz ensulφοnil / -3- / 4-ene-6- dimeτilaminο zizhdeniminοοκsi-Ι, 3, 5-τρiazin-2-yl / mοcheviny ποluchayuτ above named sοl, πρedsτavlyayuschuyu sοbοy oil osa-dok, with an output of $ 95.

Found, $: C 48, 03; Η 5.48; Cϊ 11.60; ιο ϊ8, n. σ ₂₅ n ₃₂ σι ₂ Ν ₈ ο ₅ s.

Calculated, $: 047.85; Η 5.10; 01 11.32;

Ν 17.86. Example 67.

Diethylamine ammonium salt л- / 2,6-Dichloro-benzene-15 sulfonyl / -3- / 4-dimethylamino-6-isopropodiphenidine-oxo-3,5, 3,5-τ-thiazin-2-yl / urea (compound 66).

Analogous example 53 of diethylethanolamine and Ι- / 2,6-dichlorobenzene sulfonyl / -3- / 4-dimethylamine-6-ester-reduced, has been shown to be significantly improved. It’s a natural oily garden, with a yield of $ 97.5.

Found, $: C 43.14; Η 5.19; Cϊ 11.85; Ν 19.01. Ο ^ ΟΙ ^ Z.

Calculated, $: C 43.52; Η 5, 53; Cϊ 12.26; 25 Ν 19.34.

Example 68.

Diethylammonium salt Ι- / 2, 6-dichloro-benzensulphonyl / -3- 4-dsayethylamine-6- ο ⁽ -methyl) πСΙΪ-Ι, 3, 5-τρізοш-2-connection (67). ) 30 Example 53 of dimethyl ethanolamine and

Ι- / 2, 6-dichlorobenzene sulfonyl) -3- 4-dimethylamine-6- / ο <. meson τiya / προshshidenshzhnο οκsi-1, 3, 5-τρiazsh-2-shu mοcheviny πο- luchayuτ above named sοl, πρedsτavlyayuschuyu sοbοιϊ oil οsadοκ with vyχοdοm 96.5 $. 35 Kalden, $: C 44.19; II 5.31; Cϊ 11, 51;

Ν 18.59. σ ₂₂ n ₃₄ σι ^ ₈ ο ^. - 33 -

Calculated, $: σ -44.52; Η 5.73; 0111.97;

Ν 18.89. EXAMPLE 69. 5 Diethylammonium salt Ι- / 2,6-dichloro-benzensulfonyl / -3- / 4-dimethylamine-6-benzene-m-oxy-Ι, 3,5-τ-thiazin-2-yl / urea (compound).

Similar to example 53 of diethylethanolamine and Ι- / 2, 6-dichlorobenzene sulphonate / -3- / 4-dimethylamine-6-ben- 10 osa-dok, with an output of $ 98.

Found, $: C 47.49; Η 4.85; Cϊ 10.93; Ν 17.50. C ^ Οϊ ^ 3.

15 Calculated, $: 0 47.85; Η 5.10; C1 11.32;

Ν 17.86. Example 70.

Appreciation of the great activity of the declared communications. For this purpose, a study was conducted of the depression of 20 drivers of these Ι- / 2-chlorinated benzene sulfonyl / -3- / 4-methyl-6-iodine-reduced-1,3,5-compound ) and Ι- / 2-chlorobenzene sulfonyl / -3- £ 4-dimethylamyl-6 (with methyl methyl-1,3,5-thiazin-2-yl] urine (compound 2) for both 25 and 25 κοv κuκuρuzy, οguρtsa Β uslοviyaχ labορaτορnοgο eκsπeρi- menτa ρasτeniya vyρaschivazh on ποchvaχ in sοsudaχ emκοsτyο 0.5 κg, naποzhennyχ mixture ποchva:. πesοκ: τορφ (3: 1: 1). Pρi dοvsχοdοvοm πρimenensh veschesτva vnοsizh after ποsevοm seed πuτem οπρys κivaniya ποveρχnοsτi ποchvy. Pρi 30 ποslevsχοdοvοm vnesensh οπρysκivazh ρasτeniya in φazu 2 zhsτev. Ηa κazhdy sοsud vnοsizh πο 10ml $ 0.00062 -gο πο deysτvuyuschemu veschesτvu vοdnοgο ρasτvορa, chτο sοοτveτ- sτvueτ nορme ρasχοda 20 g / ha.

Аче For the sake of reference, the use of gibber is 35 and above.

The biological activity of the appraisal of the stalk, the great bulk of the above-ground mass, the speed of manifestation - 39 -

Lunch and the growth of young people in a negative area (without soil treatment) after 3-4 weeks after processing. RETURN TO 4 VARIANT OPTIONS. The results of the experiments are presented in tables 2-4 in the $ account.

Traitor 2

Rescue of session I on the stem of the corn stalk in a dose of 20 g / ha

Account / day from the moment of withdrawal / 8 10 -ο .Ο 15 17 21

The height of the stem in $ kk on account 135 ^x 144 ^x 125 ^x 123 ^x 123 ^x 117 ^x 109

Table 3

The influence of compound I on the rate of development of young plants of corn in the dose of 20 g / ha

28 Ι53 178^х 38 173 202^х Accounting account Length of the total width / day from the moment of the upper floor of the upper floor / in% of the connection / middle of the work / in $ κ

28 Ι53 178 ^x 38 173 202 ^x

^χ - ACCESSIBLE OPTIONAL CONNECTION FOR PRINTER AND = 0.95 - 40 -

Table 4

Merger of connections I and 2 on the quantity of land mass of corn and gourmet, disposed of after 3 weeks of non-profit / loss of business

Dose of material, g / ha 1000 1000 50 20

Culture of the Corn

Next I - 114 116 142

Cultural Gourmet

Connection I 116 162 ^x 104 -

Over 2,123,132 ^x 130 ^x -

X - ACCESSORY OPTIONAL CONNECTION FOR PRINTER AND Ρ = 0.95

10 Κaκ sledueτ of dannyχ, πρivedennyχ in τablitsaχ 2 and 3, sοedshenie ι dοze to 20 g / ha sτimuliρueτ ροsτ sτeblya κuκuρuzy on ρanniχ eτaπaχ ρazviτiya mοlοdyχ ρasτeny κuκuρuzy in ρezulτaτe chegο ρazmeρy zhsτev πlasτshοκ samοgο veρχnegο on mοmenτ izmeρensh yaρusa znachiτelnοy

15 more than on end. Pο data πρivedeshym in τabzh- tse 4 usκορenie ρazviτiya προροsτκοv κuκuρuzy and οguρtsa πρivοdiτ κ τοmu, chτο ground biοmassa ρasτeny, vyρaschen- nyχ on ποchve, οbρabοτashοy sοedsheniyami I and 2, significant τelnο πρevyshayuτ biοmassu κοnτροlnyχ ρasτeny.

20 Example 71.

Estimation of the greater activity of substituted phenylsulfonyl and urinazole on the influence of them on growth - 41 -

προροsτκοv κuκuρuzy and οguρtsa. Μeτοdiκa issledοvansh analogous lοgichna οπisannοy above πρimeρe 70. During ποκazaτel usκο- ρeniya ρazviτiya προροsτκοv bρalp weight nazemnοy mass τρeχ- 5 nedelnyχ προροsτκοv οτnοsiτelnο κοnτροlya (nazezνshaya weight προροsτκοv, vyρaschennyχ on neοbρabοτannοy ποchve). Comparison of the biological activity of the compounds with close communications with the herbicide and the regulating activity of the formula

, where Ε = cι

10 (decision Α); n = СΟ ^ ΟΗ ^ (Decision B) and the herbicide GZHN (active substance that is acceptable)

as well as with the known stimulation of the growth of plants of gibber and herbicide and of stimulation of the growth of the crop of atraumus / b-isopropylamyl-2-2-2-2-2.

The results are given in table 5. - 42 -

Table 5

Already replaced fleshsulfonil-thrush and better urine for food and gourmet

Guruza

Solution

Dose in g / ha

100 20 100 20

I 116 142 ^x 162 ^x 102

2 136 ^x 130 ^x 132 ^x 125

3 128 ^x 103 96 143 ^x

4 97 104 151 ^x 109

5 106 114 98 147 ^x

6 92 136 ^x 131 ^x III

7 131 ^x 123 115 98

8 100 109 95 139 ^x

9 136 ^x 127 ^x 102 146 ^x

10 105 121 108 155 ^x

II 148 ^x 95 92 140 ^x

12 121 154 ^x 113 88

13 98 97 136 ^x 116

14 90 141 ^x 123 120

15 118 102 120 148 ^x

16 89 135 ^x 98 109

-ACTIONAL DISCONTINUITY WITH CONTROL FOR PRINTER AND Ρ = 0.95 - 43 -

Table 5

Compound ΚκκρузаΟΟΟΟΟΟ

Dose in g / ha

100 20 100 20

17 127 ^x 125 146 ^x 122

Compound Α 47 ^x 83 64 ^x 90

Unit B 31 ^x 60 ^x 20 ^x 53 ^x

Glx 0 ^x 6 ^x 0 ^x 8 ^x

Gibberells 91 101 86 95

Азτρ dose delivery

I kg / ha

123 ^x 0.5 kg / ha 114 - -

χ - ACCESSIBLE OPTIONAL CONNECTION FOR PRINTER AND = 0.95

From the data given in table 5 it follows that the claimed solutions cause the stimulation of the ground mass of food and cucumber, while it is free of

Gibber, causing the stem to grow even smaller, did not have a positive effect on the biomass of the ground part, and, as a result, our growth was disrupted.

10 applicants.

The result was identical to the one declared by the meeting, but at 10 and 25 times bigger.

Ιϊρimer 72.

The impact of sessions 52 and 53 on the environment has been studied.

15 and the development of sprouted perennial plants. The methodology for introducing the identities above is higher. Residential communications and the development of plants have been eliminated - 44 -

by weight of the biomass of the land part of the plant after 3 weeks after sowing. Immediately in the form of a water-Gzhelevsky district, it was introduced into the soil by sowing families. Results 5 are presented in table 6 as a% to the control panel (without processing of mail).

Table 6

Beyond compounds 52 and 53 on the eastern side of the building

Dose in g / ha

Βid SΟΌΗΟΓΟ plant

Connection 52 Connection 53

100 20 100 20

White white 88 97 81 105

ΙWhich is running 93 102 106 107

The best προсο 75 ^x 89 79 90

Brush 82 107 94 100

Incapable box 96 103 106 97

χ - ACCESSIBLE OPTIONAL CONNECTION FOR PRINTER AND = 0.95

From tsρivedeshyχ dashyχ sledueτ, chτο sοedineniya 52 and 53 on neznashτelnο vliyayuτ ροsτ and ρazviτie sορnyχ ρas- τeny on ρanniχ φazaχ ορganοgeneza, το esτ izbiρaτel- 10 nο sτimuliρuyuτ neκοτορye κulτuρshe ρasτeniya, sτavya iχ in bοlee vygοdnοe ποlοzhenie if κοshuρeschsh with sορ- nyaκami.

Example 73.

Evaluated the impact of the claimed compounds 52 and 53 15 on the infestation and harvest of food in the field. Indicated in the form of water-glycol products for household use and for the good entry into the soil in quantities of 20 and 50 g / ha for the active material. _ 45 -

Ilοtsad ucheτnyχ ^• delyanοκ 70 m ~, ποvτορnοsτ οbρabοτ- κi 4 κρaτnaya. Is the soil partly gray-haired, more accessible, easy-lined, containing google 1.5? ρΗ = 4.0. Нснів-

5 different home-grown species of plants at a fast-growing school: the odorless bag, the tommy bag, the lighter pepper, the middle star, the better, the better. The following results were obtained: in 1985, harvest the earth: the masses of the Ugr and used the 52nd before reaching

Soy 20 g / ha amounted to $ 149 out of turn, and for 50 g / ha - - $ 176, πριι this rate of weed fell by 98% and the final cost. As a result, the result was obtained in 1986. With this, the infestation of weeds decreased by 85% before 20 g / ha, and by 72% before 60 g / ha.

15 The weight of the land mass was 136 $ for sale (up to 50 g / ha). The effect of these compounds was to suppress in the long-term degree the same as the two-year-olds, and also the malicious people. The use of session 53 at a dose of 20 g / ha resulted in an increase in the yield of green mass.

20 baked goods per 173 kg / ha, and igra and before 40 g / ha - 86 kg / ha.

The total yield is 120 kg / ha (οСΡд ₅ = 82 kg / ha). Obviously, changing the good quality of the main part of the corn and oppressive corpses of compounds в and B in the case of non-communicable diseases (5).

25 Example 74.

It was studied the effect of coming 53 on the drought and the harvest of fresh and barley in the left in the country.

Compound 53 in the form of a one-off-the-main plant was mentioned in terms of income brought in doses of 10 and 20 g / ha

30 active material. The accounting area is 36 m, and the return is 4-fold. The soil of the plot is typical, hard to soil with a humus content of $ 4.5, ρΗ = 7.0. The main host species of foreign plants in the foreign sector are: bristles, white mother, a single

35 years old, the man of the view, the yacht is lazy, safe, the empty bag, the loin is lazy, the left is empty, the rest. The following results were obtained. Up to 10 g / ha, about 53 caused the death of $ 45 of crops in winter crops, and this resulted in a crop loss of 8.4 kg / ha. - 46 -

Standard GZHN - 2.1 kg / ha (crop at 25 kg / ha, ΗΟΡ _{η 5} - 4.0 kg / ha). On the sowing of barley, compound 53 caused the death of $ 42 and 58 species with a yield of 0 g / ha 5 and 20 g / ha, respectively. Moreover, the gain was 0.5 kg / ha and 5.2 kg / ha, respectively. Standard hl (10 g / ha)

- 2.9 kg / ha (harvest at 25.3 kg / ha, ΗСΡд ₅ -

- 2.0 kg / ha).

The best results could be better if we looked at the biological activity of the natu- ral and brown salts of the displaced fouled ones. Example 75.

It has been studied in the long run the claimed connections to the homeowner - meetings 2.9 - 11.14. 15 Ingredients in the form of an external emulsion with an active particulate matter, taken in 0.1 wt.% , and at a flow rate of working fluid of 500 l / ha, a reduction in the degree of improvement should be carried out in the process of cleaning up. The size of the accounting section is 3 m, the return is 3 20 mm. The companion of the Tashkent-л.

The results are presented in table 7.

Table 7

Comparative means of equipments containing substituted urine of general formula

πο влиянию на уροжаи χлοша-сыρца

πο influence on the health of the raw-raw

Immediate Conclusions Ε ² κ ¹ Y ³ Y ⁴

2 Η Сϊ σн ₃ 9 Η сο ₂ σн ₃ σн ₃ ^С 2 ^Η 5 - 47 -

Offer 7

Immediately

] & Connections Ε ² Ε ¹ Η ³ Ε ⁴

10 Η σο ₂ sn ₃ Η ^C 6 ^Η 5

II π 1 сο ₂ sn ₃ n С _β Η ^ Сέ! -2

14 C1 C1 n ^C 6 ^Η 5

March

Delivery table 7

Dose, g / ha

^} £ Compounds 10 50 100 kg / ha κ nto. $ ts ha κ account $ $ ts / ha ^ _ont

2 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

10 28 D 101.7 26.6 96.4 34.6 125.3

II 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

Late 27, 6

Note: ΗСΡд ^ = 9.6 q / ha - 48 -

Intended use

The claimed compounds are displaced phenylsulfonylazinous and they are also involved in the 5 substances of the claimed funds for the stimulation and the reduction of welfare.

Claims

- 49 - ΦΟШШ. I30BΡ2ΤΞΗIYA I. Substituted fühsulfünltrühlung and shih saluy general formula:

Where κ ¹ = cι, ΝΟ, σοοσнο Κ ² = Η, (3. κ ³ = n, σn ₃ Κ = СΗο, С Η, -, σ, СρΑл Сϊ —2 and not available or s ₂ n ₅ χ = Κ, Νа, ΗЖ С ₂ Η ₅ s ₂ n ₄ οн 5 2. Sρedsτvο for sτimuliροvashsh and ποdavleniya ροsτa ρasτeny, sοdeρzhaschee deysτvuyuschee veschesτvο and ρazbaviτel, χaρaκτeρizuyuscheesya τem, chτο in κachesτve deysτvuyuschegο of Great schesτva οnο sοdeρshιτ substituted φeshιlsulφοnilτρiazshshl- mοchevish IL iχ sοzh πο π.Ι. 10 3. Sρedsτvο for sτimuliροvaniya and ποdavleshιya ροsτa ρasτenshϊ πο π.2, χaρaκτeρizuyuscheesya τem, chτο in κachesτve deysτvuyuschegο veschesτva οnο sοdeρzhiτ Ι- / 2-χlορbenzensul- φοnil / -3- / 4-diιντeτil zhnο-6-izοπροπizhdeniminοοκsi-1, 3 , 5- -τρiazsh-2-yl / urea or its urea, sodium, concrete 15 diethylaminamine salt of the general formula: - fifty -

where χ is absent or / ^С 2 ^Η 5 χ = Κ, Νа, ΗΛ / s ₂ n ₅ s ₂ n ₄ on 4. Means for stimulating and suppressing the pressure of products are subject to π.2, which is growing in that, in fact, it is in good condition that the connection is in good condition. -labeled / ρ ρ-жд ени ени ени ени 3,5 3,5 3,5 Ι τ, 3,5-ρ ρ ин ин ин ин]]] urea and its urea, sodium, urea and ethylenediamine salt of the general formula:

where χ - there is no IL ₂ n ₅ χ = κ, Ηа, нι- / σ ₂ n ₅ σ ₂ n ₄ on