DE2225773A1 - Triazines and processes for their manufacture - Google Patents

Description

input-! jcTgen m ... jS.ψ

Dr. F. Zumsteln sen. · Dr. E. Assmann Dr. R. Koenlgsberger - Dlpl.-Phys. R. Holzbauer - Dr. F. Zumsteln Jun.

PATENT LAWYERS

TELEPHONE: COLLECTIVE NO. 225341

TELEX 529979

TELEGRAMS: ZUMPAT CHECK ACCOUNT: MUNICH 91139

BANK ACCOUNT: BANK H. HOUSES

8 MUNICH 2.

BRÄUHAUSSTRASSE 4 / III

xc / n Cas 1463 f / d

ROUSSEL UCLAF, Paris / France

Triazines and processes for their preparation

The invention relates to new triazines and a process for the preparation of these compounds.

The invention relates in particular to the triazines of the general formula I

RHN

-CH

wherein

X is a chlorine atom or the group of the formula SCH ₃ , R "is a hydrogen atom or the group R ¹ ,

R and R ¹ , which can be identical or different, straight = chain or branched alkyl radicals with 1 to 5 carbon atoms and

η denote the number 1 or 2.

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The invention thus relates to triazines, the general Formulas I »and I,

H ₂ ) _n

and

K
^l "-A _W ^ R ·. ¹ B

correspond, in which X, R, R ¹ and η have the meanings given above.

The alkyl group is in particular a methyl, ethyl, propyl, isopropyl, butyl or tert-butyl group.

Particularly preferred compounds of the general formula I are the following:

2-isopropylamino-4- (2'-tetrahydropyranyl) -amino-6-chloro-1,3,5-triazine,

2-isopropylamino-4- (2'-tetrahydropyranyl) -amino-6-methylthio-1,3,5-triazine,

2-isopropylamino-4- [N'-methyl-N '- (2'-tetrahydropyranyl) -amino] -6-chloro-1,3,5-triazine,

2-Isopropylamino-4- [N'-methyl-N '- (2'-tetrahydropyranyl) -amino J-6-methylthio-1,3,5-triasin,

2-ethylamino-4- [N ^ methyl-N '- (2' -tetrahydropyre-Ryl · -) - <üaiino] -6-chloro-1,3,5-triazine,

2-Ethylair! Ino-4 ~ [N'-methyl-N '- (2' -tetrahydropyranyl) -amino] -6-

209851/12 4 5

methylthio-l, 3,5-triazine,

2-Xthylamino-4- [N'-ethyl-N'-12'-tetrahydropyranyl) amino] -6-chloro-1,3,5-triazine and

2-Ethylamino-4- [N ^f -ethyl-N '- (2'-tetrahydropyranyl) -amino] -6-methylthio-1,3,5-triazine.

The compounds of general formula I have remarkable herbicidal pre-emergence and post-emergence properties, the make them suitable for combating weeds in agriculture.

The herbicidal properties of these compounds can be determined by studies on representative plants of the great botanical Families like oats, wheat, maize, foxtail grass (Graminaceae), the beetroot (Chenopodiaceen), the Chrysanthemum (Composaceae), the clover (Papilionaceae), the Flax (Linaceae) and mustard (Cruciferaceae) are shown. The results of these studies are given below.

The invention also relates to a process for the preparation of the new triazines of the general formula I _1, which is characterized in that

either a 2-alkylamino-4-amino-6-chloro-IjS ₁ S-triazine of the general formula II.

RHN '

¹¹ A

wherein R has the meaning given above, with a compound of the general formula III,

III

where η has the meaning given above, condensed, so

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that a compound of the general formula I »

(Formula I '= Formula I, where X = Cl and R "■ H

_fiHIi ^ ^ _ .. 'r> mean)

CH ₂ ) _n

obtained, in which R and η have the meanings given above, or

a 2-alkylamino-4,6-dichloro-1,3,5-triazine of the general formula II _ß

Cl

¹¹ B

R-HN Sr ^ Cl

wherein R has the meaning given above, with an amine of the general formula Hin

¹¹¹ B

in which R ¹ and η have the meanings given above, condensed so that a compound of the general formula I * _B

Cl

(Formula I »Formula I,

Λ ι where X - ⁰ Cl and R "« R ·

jy ^ v / R ¹ mean)

dd

CH ₂ ) _n

obtained, in which R, R ¹ and n. have the meanings given above, and if desired, a compound of the general formula 1 '^ or a compound of the general formula I' _B

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with an alkali metal or ammonium thiomethylate, so that a compound of the general formula I ".

SCR

(Formula I "= Formula I, where X = SCH ₃ )

obtained, in which R, R "and η have the meanings given above.

The invention also relates to herbicidal compositions which, as the active ingredient, contain one or more compounds of the general Formula I included. These compositions can be in the form of powders, granules, suspensions, emulsions or solutions which contain the active ingredient, for example, together with a carrier material and / or a cationic, anionic or nonionic surfactant, which forms a uniform dispersion which ensures the components of the composition contain. The carrier material used can be a liquid such as Water, alcohol, a hydrocarbon or another organic solvent, a mineral, animal or vegetable Oil or a powder such as talc, a clay, a silicate or diatomaceous earth.

The solid compositions, which may be in the form of a dust powder, a wettable powder, or a granulate by rubbing the active substance with an inert solid or by impregnating the solid carrier material with a solution of the active ingredient in a solvent, which is then evaporated.

The compositions can optionally contain other pesticides, herbicides, fungicides, biocides, insecticides etc. and substances that influence the growth of plants.

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The compositions are, of course, employed in amounts sufficient to achieve the herbicidal effects will. The doses of the active ingredient in the compositions vary depending on the plants to be destroyed, the type of soil, the atmospheric conditions and the state of growth of the vegetation to be destroyed.

The invention also relates to the use of the invention Compositions which contain at least one compound of the general formula I as the active ingredient, for Extermination of weeds.

The following examples are intended to explain the invention further without, however, restricting it.

example 1

2-Isopropylamino-4- (2'-tetrahydropyranyl) -amino-6-chloro-1,3,5-triazine

3 7.5 g of 2-isopropylamino-4-amino-6-chloro-1,3,5-triazine are brought in a solution containing 5 g of p-toluenesulfonic acid, 20 ecm Contains 2,3-dihydropyran and 500 ecm tetrahydrofuran. The received The solution is refluxed for 3 hours with stirring at a temperature of about 90 ° C. and then stirred for 16 hours at room temperature. The solvent is evaporated to dryness under reduced pressure A resin is obtained which is chromatographed on silica [eluent: benzene / ethyl acetate (7/3)], and is obtained 18 g of 2-isopropylamino-4- (2'-tetrahydropyranyl) -amino-6-chloro-1,3,5-triazine in the form of an oil.

ArIaIy _- séj _- C ₁₁ H ₁₈ ClN ₅ O = 271.73

Calculated: C 48.62 H 6.68 Cl 13.05 N 25.78% Found: 49.2 6.7 12.1 23.7%

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Example 2

2-Isopropylamino-4- (2'-tetrahydropyranyl) -amino-6-methylthio-1,3,5-triazine

In a solution containing 60 g of 2-isopropylamine-4- (2 * -tetrahydropyranyl ) -amino-6-chloro-1,3,5-triazine in 600 ecm tetrahydrofuran contains, a suspension is added which contains 31.2 g of sodium thiomo in 400 ecm of tetrahydrofuran. The preserved sus-

pension is stirred ^{at 25 to 30 °} C. for 4 hours and 30 minutes. The sodium chloride formed is then removed by filtration and the filtrate is evaporated to dryness under reduced pressure. The oil obtained is chromatographed over silica [eluent: benzene / ethyl acetate (4/6)]. In this way, 30.5 g of 2-isopropylamino-4- (2'-tetrahydropyranyl) -amino-6-methylthio-1 are obtained , 3,5-triazine.

Analysis; ^C ₁₂ ^H 21 ^N 5 ^{OS =} 283.398

Calculated: C 50.86 H 7.47 N 24.71 S 11.32 % Found: 51.1. 7.4 23.8 10.7 %

• *

Example 3

2-Isopropylamino-4- [N · -methyl-N · - (2 ♦ -tetrahydropyranyl) -amino] -

6-chloro-1,3,5-triazine

41.2 g of 2-isopropylamino-4j6-dichloro-1,3,5-triazine are introduced into 500 ecm of tetrahydrofuran, stirred until completely dissolved and then 500 ecm of chloroform are added while maintaining a temperature of 20 ° C. After cooling to ⁰ ° C., 46 g of N-methyl-N- (2-tetrahydropyranyl) amine and 300 ecm of chloroform are added to the mixture over the course of 20 minutes while maintaining this temperature.

The mixture is stirred for 64 hours at 20 ° C. and then evaporated to dryness under reduced pressure. The residue is chromatographed on silica, eluting with a mixture of benzene and acetone (3/7). In this way you get 50 -? 2-Isopropylamino-4- [N ¹ -methyl-N '- (2'-tetrahydropyranyl) -aminoJ-6-chloro-1,3,5-triazine in the form of a white syrupy paste

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Liquid which slowly crystallizes out and which is soluble in xylene, cyclohexanone and acetone and sparingly soluble in water. F <6O ⁰ C.

^c i2 ^H 2O ^C1N 5 ° ^{= 285} > ⁷⁸

Calculated: C 50.43 H 7.05 Cl 12.41 N 24.51 % Found: 50.9. 7.1 12.1 24.0 %

By reacting N-methyl-N- (2-tetrahydrofuranyD-amine) one obtains in an analogous manner with 2-isopropylamino-4,6-dichloro-1,3,5-triazine 2-isopropylamino-4- [N'-methyl-N '- (2'-tetrahydrofuranyl) -amino] -6-chloro-1,3 , 5-triazine.

Example 4

2-Isopropylamino-4- [N'-methyl-N '- (2' -tetrahydropyranyl) -amino] -6-methylthio-1,3,5-triazine

25 g of 2-isopropylamino-4- [N ¹ -methyl-N '- (2'-tetrahydropyranyl) -amino] -6-chloro-1,3,5-triazine in 150 ecm of ethanol are added and then 750 ecm of one is added I, 3N sodium methyl mercaptan solution in ethanol is added. The mixture is stirred at 20 ° C. for 65 hours. The sodium chloride precipitate formed is then filtered off and washed with ethanol. The ethanol filtrates are combined and evaporated to dryness under reduced pressure. The residue is taken up in ethyl acetate and the suspension thus obtained is washed with water, dried, filtered and evaporated to dryness under reduced pressure. In this way, 21.5 g of 2-isopropylamine-4- [N ^f -methyl-N '- (2'-tetrahydropyranyl) amino] -6-methylthio-1,3,5-triazine are obtained in the form of a weak -yellow, resinous oil that is soluble in xylene and cyclohexanone and sparingly soluble in water.

Analysis: C ₁₃ H ₂₃ N ₅ OS = 297.42

Calculated: C 52.48 H 7.80 N 23.54 S 10.79% Found: 52.7 7.9 23.1 9.2%

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It is produced in an analogous manner by reacting sodium methyl mercaptan with 2-isopropylamino-4- [N'-methyl-N · - (2'-tetrahydrofuranyl) -amino] -6chlor-1, 3,5-triazine 2-Isopropylamino-4- [N · -methyl-N '- (2'-tetrahydrofuranyl) -amino] ~ 6-methylthio-lj3,5-triazine here.

Example 5

2-ethylamino-4- [N'-methyl-N · - (2'-tetrahydropyranyl) -amino] -

6-chlorine-l _? 3,5-triazine

One gives 117.7 g of 2-Xthylamino-4,6-dichloro-l, 3,5-triazine in 1,200 cc of tetrahydrofuran, the mixture is stirred until complete dissolution and cooled to -20 ⁰ C · is then added dropwise with stirring while maintaining a temperature of -20 C a solution of 70 g of N-methyl-N- (2-tetrahydropyranyl) amine in 850 ecm of tetrahydrofuran, which contains 61 g of triethylamine, added. The temperature is allowed to rise to 20 ^° C. and the mixture is stirred overnight. The triethylamine hydrochloride formed is filtered off with suction and the filtrate is evaporated under reduced pressure. The residue is taken up with 150 ecm of a benzene / ethyl acetate mixture O / l), the insoluble materials are filtered off and the piltrate is left to stand overnight. The crystals formed are filtered off with suction and recrystallized from 300 ecm of isopropyl ether. This gives 74 g of 2-ethylamino-4- [N'-methyl-N '- (2'-tetrahydropyranyl) amino] -6-chloro-1,3,5-triazine in the form of white crystals which melt at 114 ° C.

Analysis:. C ₁₁ H ₁₀ ClN ^ -O = 271.75

Calculated: C 48.61 H 6.68 Cl 13.05 B 25.77 % Found: 48.5 6.7 13.3. 25.6 %

Example 6

2-Xthylamino-4- [N'-methyl-N '- (2'-tetrahydropyrany l) -amino] - 6-methylthio-1,3,5-triazine

A solution of is added to a suspension of 25 g of sodium methyl mercaptan salt in 240 ecm of tetrahydrofuran with stirring 50 g of 2-ethylamino-4- [N'-methyl-N · - (2'-tetrahydropyranyl) -amino] -

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6-chloro-1,3,5-triazine in 450 ecm tetrahydrofuran. The mixture is stirred overnight at room temperature and then for 8 hours at 40 ° C. and finally overnight at room temperature. The sodium chloride precipitate formed is filtered off and the filtrate is treated with 1300 ecm of ether. The organic phase is washed with water, with sodium hydroxide solution and with water until neutral. The solvents are evaporated off under reduced pressure and an oily residue is obtained which crystallizes on trituration with petroleum ether. Recrystallization from isopropyl ether gives 14.6 g of 2-ethylamino-4- [N ¹ -methyl-N '- (2 ⁽ -tetrahydropyranyl) -amino] -6-methylthio-1,3,5-triazine in the form of white Crystals that melt at 86 ° C.

Analysis; C ₁₂ H ₂₁ N ₅ OS = 283.40

Calculated: C 50.85 H 7.47 N 24.72 S 11.31 % Found: 51.0 7.5 24.6 11.0%

Example 7

2-Xthylamino-4- [N'-ethyl-N ^t - (2'-tetrahydropyranyl) -amino] -6-chloro-1,3 ₁ 5-triazine

One gives 117 g of 2-Xthylamino-4,6-dichloro-l, 3,5-triazine to 1200 cc of tetrahydrofuran, dissolved with stirring and then cooled to -20 ⁰ C. A solution of 79 g of N-ethyl-N- (2-tetrahydropyranyl) amine in 850 ml of tetrahydrofuran, which contains 61 g of triethylamine, is then added dropwise with stirring at this temperature. The temperature is allowed to rise to 20 ° C. and the mixture is stirred for a further 16 hours. The reaction mixture is then taken up in 2 liters of ethyl acetate, washed with water, the organic phase is dried over sodium sulfate and then evaporated to dryness under reduced pressure. The residue is taken with 500 cc of methanol and obtains 100 g 2rÄthylamino-4- [N ^l -ethyl-N '- (2'-tetrahydropyranyl) amino] -6-chloro-l, 3,5-triazine in the form of white crystals that melt at 145 ° C.

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Analysis: C ₁₂ H ₂₀ ClN ₅ O = 285.75. -

Calculated: C 50.43 H 7.05 Cl 12.42 N 24.53 % Found: 49.8 7.0 12.5 25.1 %

Example 8

2-Ethylamino-4- [N'-ethyl-N '- (2'-tetrahydropyranyl) -amino] -6-methylthio-1,3,5-triazine

To a suspension of 12 g of 2-ethylamino-4- [N'-ethyl-N '- (2 · - tetrahydropyranyl) amino] -6-chloro-1,3,5-triazine in 40 ecm tetrahydrofuran and 25 ecm of ethanol are added dropwise with stirring 30 ecm of a solution of 3.5 g of sodium methyl mercaptan salt in ethanol. The mixture is stirred for a further 16 hours at room temperature. The reaction mixture is then taken away 150 ecm of chloroform, washed with water, dried the organic Phase over sodium sulfate and evaporated under reduced Pressure to dryness. The residue is chromatographed on silica by treating with a benzene / ethyl acetate mixture (9/1) eluted. In this way, 8 g of 2-ethylamino-4- [N'-ethyl-N '- (2'-tetrahydropyranyl) -amino] -6-methylthio-1,3,5-triazine are obtained in the form of a yellow oil.

NMR spectrum

Signal corresponding to the methylthio group at 149 Hz, signals corresponding to the ethyl group triplets at 64.5, 72, 79, 66.5, 73.5 and 80.5 Hz,

signal corresponding to the NH proton at 320 Hz, corresponding to the angular proton of the tetrahydropyranyl radical Signal at 355 Hz,

the ß- and f -ethylene groups of the tetrahydropyranyl residue corresponding signals at 80 and 130 Hz,

Signals at 194 and 250 Hz, those in the α-position to the tetrahydropyranyirest standing methylene group and the ethyl group quadruplets correspond.

209851/124 5,

Investigation of the herbicidal effect

The nine plants used (oats, beetroot, wheat, chrysanthemum, flax, corn, mustard, clover and foxtail grass) are cultivated in culture tubs (23 × 14 × 4 cm) with a double bottom, which are watered from below. The nine plant species are each planted with 20 seedlings in rows with a distance of 3 cm in a single tub, with four experiments being carried out for each concentration of the active ingredient. The culture conditions are as follows: Temperature: 20 ° C + 2 ° C
Humidity: about 60 %

Illumination by fluorescent tubes (daylight and bright white light) from 6 a.m. to 10 p.m. daily. The soil mixture used consists of 10 volumes of soil, 10 volumes of river sand and 2 volumes of peat.

For pre-emergence examinations, treatment is carried out 24 hours after sowing and the first irrigation is carried out Sprinkle some of the product in the area of the seeds bring to.

In the case of post-emergence examinations, treatment is carried out after 21 days of cultivation on the parts protruding from the soil of the plants.

In both cases, the product to be examined is shown below Standard conditions using a micro-nebulizer with doses ranging from 5 to 0.625 kg / ha, applied at a dilution corresponding to 500 l / ha «

Comparative examinations without treatment are also carried out. The final evaluation is made by weighing the plants 21 days after treatment in the case of the pre-emergence examinations and 15th days after treatment in the case of the post-emergence examinations.

The results are given as a percentage of the vegetation reduction P:

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Weight of the reference plant - Weight

of the treated plants ρ "- - χ

Weight of the reference plants

In the following 2-isopropylamino-4- [N ^l -methyl-N '- (2 · - tetrahydropyranyl J-aininoJ-e-inethylthio-l ^ jS-triazine as compound A, 2-ethylane »ino-'4- [N ¹ -methyl-N '- (2'-tetrahydropyranyl) -amino] -6-methylthio-1,3,5-triazine as compound B and 2-isopropylamino-4- {2 • -tetrahydropyranyl) -amino-6 -methylthio-1,3 _f S-triazine referred to as compound C.

a) Pre-emergence examinations:

• · · Percentage of vegetation reduction 2.5 78 7th Connection B 2.5 1.25 OfiS ! Connection C dose
(kg active ingredient / ha] Connection A 100 28 0 5 100 80 € 9 2.5 oats 5 38 ■
0 0 ! 00 48 0 0 50 wheat 100 0 60 30th 67 0 0 0 50 Corn 55 75 100 25th 96 91 0 0 Foxtail grass 0 100 10C 100 1OC 100 100 Beetroot 93 1OC 100 100

Chrysanthemum 100 100 100 100 100 100 100 100 100 flax 100 100 100 71 100 100 100 90 50 mustard 100 100 100 100 100 100 100 100 100 Clover '; 100 100 100 100 10C 100 100 100 100

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Post-emergence examinations;

Percentage of vegetation degradation 2.5 1.25 0.625 Connection B 2.5 1.25 0.625 Conn. C. Disus
(kg active ingredient / ha) Connection A 100 40 30th 5 100 100 59 2.5 oats 5 86 εο 30th 100 82 60 0 100 wheat 00 30th 20th 0 89 30th 10 5 50 Corn K) O 100 100 50 82 100 87 65 50 Foxtail grass 60 100 100 100 100 100 100 100 100 Beetroot 00 100 100 75 100 10C 100 100 100 Chrysanthemum 100 100 10C 100 100 100 10C 55 50 flax 100 100 10C 25th 100 10C 100 100 50 mustard 100 100 100 100 10C 10C 100 100 100 clover 100 ία 50 100

Result:

The compounds A, B and C have interesting herbicidal properties. Destroy even at a dose of 0.625 kg / ha the connections A and B the weeds almost completely. At this dose, the Gramineae remain practically unaffected.

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Herbicidal composition based on 2-isopropylamino - 4- (2 '-tetrahydropyranyl j-amino-e-methylthio-1,3 ₁ 5-triazine

The ingredients indicated below are mixed., Bis a homogeneous liquid concentrate is obtained:

2-isopropylamino-4- (2'-tetrahydropyranyl) -amino-

6-methyl-1,3,5-triazine 25 %

Atlox 4851 ⁺⁾ 6.4 %

Atlox 4855 ⁺⁺⁾ 3.2%

Xylene 65.4 %

+) Mixture of an alkylarylsulfonate and a triglyceride of polyoxyethylene, viscosity at 25 ° C 300 to 700 centipoise.

++) Mixture of an alkylarylsulfonate and a triglyceride from Poly
tipoise.

of polyoxyethylene, viscosity at 25 ° C 1500 to 1900 Cen-

Mixed to make a composition to be atomized the concentrate with water, the amount of water added depending on the dose of the active ingredient to be used.

You work in the same way, for example if you use a herbicide Composition based on 2-isopropylamino-4- [N'-methyl-N '- (2'-tetrahydropyranyl) -amino] -6-methylthio-1,3,5-triazine wants to manufacture.

209851/1245

Claims (14)

- 16
Claims wherein X is a chlorine atom or a group of the formula SCH. ,, R "is a hydrogen atom or a group R ', R and R ¹ , which can be identical or different, represent a straight-chain or branched alkyl radical having 1 to 5 carbon atoms and η denote the number 1 or 2. 2.) Triazines of the general formula I. 'η in which ' X is a chlorine atom or the group of the formula SCH-, R is a straight-chain or branched alkyl radical with 1 to 5 carbon atoms and. / '. η is the number r or 2 i · '.; mean. ORIGINAL 209851/1245 3.) Triazines of the general formula wherein X is a · chlorine atom or the group of the formula SCH. ,, R and R ', which can be identical or different, represent a straight-chain or branched alkyl radical with 1 to 5 carbon atoms and η is the number 1 or 2
mean. 4.) 2-Isopropylamino-4- (2'-tetrahydropyranyl) -amino-6-chloro- ■ 1,3,5-triazine. 5.) 2-Isopropylamino-4- (2'-tetrahydropyranyl) -amino-6-methylthio-1,3,5-triazine. 6.) 2-Isopropylamino-4- [N'-methyl-N ^f - (2'-tetrahydropyranyl) -amino] -6-chloro-1,3,5-triazine. 7.) 2-Isopropylamino-4- [N'-methyl-N ^l - (2'-tetrahydropyranyl) -amino] -6-methylthio-1,3,5-triazine. . 8.) 2-Ethylamino-4 '- [N'-methyl-N' - (2'-tetrahydropyranyl) -amino} -6-chloro-1,3,5-triazine. 9.) 2-Xthylamino-4- [N'-methyl-N '- (2'-tetrahydropyranyl) -amino] -6-methylthio-1,3,5-triazine. 10. ) 2-Ethylamino-4- [ N · -ethyl-N · - ( 2'-tetrahydropyranyl) -amino] -6-chloro-1,3,5-triazine. 209851/1245 - entrances M ² Wj ^ L 11.) 2-Ethylamino-4- [N ^f -ethyl-N '- (2'-tetrahydropyranyl) -amino] -6-methylthio-1,3,5-triazine. 12.) Herbicidal compositions, characterized in that they are as active ingredient at least one compound according to claims 1 to 11 included. 13.) Use of the compositions according to claim 12 for combating of weeds. 14.) Process for the preparation of the triazines of the general formula I. (i) RHN ' I— CH ^) 2'n wherein X is a chlorine atom or the group of the formula SCH-, R "is a hydrogen atom or the group R ¹ , R and R ¹ , which can be identical or different, represent a straight-chain or branched alkyl group having 1 to 5 carbon atoms and η is the number 1 or 2 mean, characterized in that one either a 2-alkylamino-4-amino-6-chloro-1,3,5-triazine of the general formula II. (H ₁ ) j. " ^ i RHN ' in which R has the meaning given above, with a compound of the general formula III _A 209851/1245 (ιιϊ _α ) in which η has the meaning given above, condensed so that a compound of the general formula I *. {Formula I '= Formula I, where X = Cl and R "= H) L- (CH ₂ : obtained, in which R and η have the meanings given above, a 2-alkylamino-4,6-dichloro-1,3,5-triazine of the general 'Formula II, Cl R-HK ^K Cl - wherein R has the meaning given above, mit.einem amine of the general formula ΙΙΙ _β I- t in which R ¹ and η have the meanings given above, condensed so that a compound of the general formula I 20985 1/1 2 A 5 i ( ι nt ^R ' ^mean) »/ ^^ ii (Formula I ' _R = Formula I, r nt where X = Cl and R "= obtained in which R, R ¹ and η have the meanings given above, and if desired, the compound of the general formula I ¹ or the compound of the general formula I 'is reacted with an alkali metal thiomethylate or ammonium thiomethylate, so that a compound of the general formula I is reacted " . SOH ₃
jf ^ N (Formula I "= Formula I, where X = SCH ₃ ) obtained, in which R, R "and η have the meanings given above. 209851 / 1245-