CH633411A5 - Herbicidal composition and process for the preparation of novel 1-benzothiazolylimidazolidinones - Google Patents

Description

The invention relates to a herbicidal composition which is characterized in that it is a new 1-benzothiazolylimidazolidinone of the formula I as active ingredient

Ü

i ch—: ch

M

alkyl group, a cycloalkyl group or a group of the formula

H (5-m)

30th

&

\

, c - n

- (ch2) p

H

(4-n)

No

\ / 35

C.

I!

0 (l)

contains what

X represents an alkyl group, a halogen atom, a halogenated alkyl group or an alkoxy group,

n is 0.1 or 2,

R1 is an alkyl group, an alkenyl group, a halogenated alkyl group or a group of the formula

R4

- C - C "= CK

r-

50

60

means and where

R4 and Rs independently of one another represent hydrogen atoms or alkyl groups, and

Q has the following meanings:

(1) a hydroxyl group,

(2) an amine group of the formula

R2

1 3

- NO

wherein R2 and R3 independently of one another are a hydrogen atom, an alkyl group, an alkenyl group, a halogenated alkyl group, a hydroxyalkyl group, an alkoxy group

mean, where p = 0 or 1,

m = 0 or an integer in the range from 1 to 3, and

Y represents an alkyl group, an alkoxy group, an alkylthio group, a halogen atom, a halogenated alkyl group, a nitro group or a cyano group, or (3) an ester group of the formula:

O

H 6

- O - C - Rb, in which

R6 is an alkyl group, an alkenyl group, a halogenated alkyl group, a hydroxyalkyl group, an alkynyl group, an alkoxyalkyl group, a cycloalkyl group or a group of the formula

?(5 m)

- (ch2) p

means, in this formula p = 0 or 1,

m = 0 or an integer in the range from 1 to 3, and

Y represents an alkyl group, an alkoxy group, an alkylthio group, a halogen atom, a halogenated alkyl group, a nitro group or a cyano group.

633 411

6

New compounds of the formula

OH

I.

CH-

CH-

II

\

C - N

N - RJ

(II),

H (4-n)

wherein the substituents are defined above, are prepared according to the invention by using a compound of the formula

Ï

X

n

H

(4-n)

%

H

I.

OCH

i 3

C-N'-C-N - CH2 ~ CH

li I

I.

OCH-

(IV)

cyclized to the compound of formula II. The new compounds of the formula qn

CH CH-

* n

V

NUMBER 1

H,

(Ia)

C - N

s / \ /

C.

II

(4-n) 0

wherein Q 'is a group of the formula

R2 I o -N-R

are obtained according to the invention by first preparing compounds of the formula II and then using ammonia or an amine of the formula

R

H-N-R

implements.

Other new compounds of the formula

Qu wherein Q "is an ester group of the formula -O-S-R6

represents, according to the invention are also obtained compounds of formula II by reaction with a 35 acid of the formula

R6-COOH

or a reactive functional derivative of this acid.

The new compounds have a high herbicidal activity.

In preferred new compounds of formula I 45 X is an alkyl group with 1-6 carbon atoms optionally substituted with chlorine or bromine, a trifluoromethyl group, an alkoxy group with 1-6 carbon atoms, a chlorine atom or bromine atom,

n is 0.1 or 2, so R1 is an optionally halogen-substituted alkyl group with 1-6 carbon atoms, an alkenyl group with up to 6 carbon atoms or a group of the formula:

55

CH-

-CH.

H

V

- C - C-.

R-

: CH

60

(4-n)

JC - N N-R1,

\ /

C.

II o

(Ib)

wherein

R4 and R5 independently of one another denote hydrogen atoms or alkyl groups with up to 3 carbon atoms,

65 R2 and R3 are independently hydrogen atoms, alkyl, haloalkyl, hydroxyalkyl or alkoxyalkyl groups each having 1 to 6 carbon atoms in the alkyl part, alkenyl groups having up to 6 carbon atoms,

7

633 411

Cycloalkyl groups with 3 to 7 carbon atoms or groups of the formula h (5-m)

- <ch2) p where p = 0 or 1,

m = 0 or an integer in the range from 1 to 3,

Y is an alkyl, alkoxy, alkylthio, chloroalkyl or bromoalkyl group each having 1 to 6 carbon atoms in the alkyl part, the trifluoromethyl group, a halogen atom, the nitro group or the cyano group,

R6 is an alkyl, haloalkyl, hydroxyalkyl or alkoxyalkyl group each having 1 to 6 carbon atoms in the alkyl part, an alkenyl group having up to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms or a grouping of the formula

- (ch2)

means where m, p and Y are defined above.

The reaction of compounds of formula II with an amine of formula III

R ^

h - n - r wherein in this formula R2 and R3 are as defined above, is preferably carried out by the compound of the formula II with about an equimolar amount or with a molar excess of the amine of the formula III in an inert reaction medium, such as Example heptane or toluene, brings together and then the reaction mixture is heated with stirring until the reflux temperature is reached and the water of reaction is removed azeotropically. The reaction mixture can then be cooled and the desired product can be obtained by filtration if a precipitate forms or by evaporation of the organic reaction medium if the compound is soluble in it. The product can then be purified by conventional procedures, such as recrystallization or the like.

The compounds in which Q "is a group of the formula

0

"I 6 - 0 - C - Rd can preferably be prepared by the compound of formula II with an acid chloride of formula VIII

0

Cl - c -

IV

(viïi)

5 being in this formula

R6 is as defined above in the presence of an acid acceptor such as a tertiary amine. This reaction can be carried out by very slowly stirring the acid chloride of formula VIII to a solution of an approximately equimolar amount of the compound of formula II in an inert organic solvent in the presence of an acid acceptor at a temperature of from about 10 to about 30 ° C adds. After the addition is complete, the reaction mixture can be heated up to a temperature at which reflux occurs to ensure the completion of the reaction. The desired product can then be obtained by first filtering the reaction mixture to remove the acid acceptor chloride and then evaporating the solvent if the product is soluble in it, or if it occurs in the form of a precipitate, by filtration and then washing and cleaning .

These compounds can preferably also be prepared in the white by combining a compound of the general formula II with an acid anhydride of the formula IX

30th

R

O

! l

- C

- O

0

Ii c -

R

(ix)

being in this formula

R6 is as defined above, in the presence of a catalytic amount of p-toluenesulfonic acid. This reaction can be carried out by bringing the reactants 35 and the catalyst together at room temperature in an inert organic reaction medium and then heating the reaction mixture on the water bath with stirring for a period of about Vi to 4 hours. The reaction mixture can then be cooled 40 and the desired product isolated by filtering if it occurs as a precipitate or by evaporating the organic reaction medium if it is soluble in it. In some cases, the acid anhydride can be used as a solvent for the compound of formula II, making the use of an inert solvent as a reaction medium unnecessary. When lower carboxylic acid anhydrides are used, water can be added to the reaction mixture to precipitate the desired product after the reaction is completed. The product can then be purified by conventional procedures such as recrystallization and the like. In some cases, the above-mentioned reaction leads to a product mixture consisting of the desired compound and dehydrated starting material of the general formula X.

65H (4 "n)

consists in this formula

X, n and R1 are as defined above.

633411

In these cases, the desired product can be isolated by fractional precipitation.

The compound of formula II can preferably be easily prepared by using the compound of formula IV

H

I.

N-

C.

II

O

OCH.

- N - CHo - CH

r1

i

OCH

(IV)

(4-n)

being in this formula

X, n and R1 are as defined above, heated in a dilute acidic reaction medium for a period of about 10 to about 60 minutes. Temperatures from about 60 ° C to the reflux temperature of the reaction mixture can be used. The reaction medium may contain a dilute aqueous inorganic acid such as hydrochloric acid in a concentration of about 0.5 to about 10%. Water-miscible lower alkanols can also be suitably added to the reaction medium to improve the solubility of the starting material. After completion of the reaction, the desired product can be obtained by evaporating off the solvents used, if they are soluble in them, or by filtration, if they occur in the form of a precipitate. This product can then be used as such, or it can be further purified by conventional procedures such as leaching, recrystallization, washing and the like. Compounds 20 of Formula IV can be prepared by mixing a molar amount of an isocyanate dimer of Formula V

X

n yts

G4-n)

C - M = C = O

H

being in this formula

X and n are as defined above, with about two molar amounts of a dimethyl acetal of formula VI

(V)

H - N - CH "-

R

OCH.,

1 year

CH I

OCH «

(VI)

being in this formula

R1 is as defined above. This reaction can be carried out by contacting the isocyanate dimer of formula V in an inert organic solvent such as benzene with the acetal of formula VI at room temperature and stirring the mixture so obtained for a period of from about Vi to 4 hours. The reaction mixture can then be filtered and the solvent is usually evaporated from the filtrate to give the desired product. This product can then be used as such or after further purification by conventional procedures.

The isocyanate dimer of formula V can be prepared by using a benzothiazole of general formula VII

n

.N

^ C - NH,

H

(4-n)

(VII)

wherein in this formula 35 X and n are as defined above, reacted with phosgene. This reaction can be carried out by adding a slurry or a solution of the benzothiazole in a suitable organic solvent such as ethyl acetate to a solution of phosgene in a similar solvent. The mixture so obtained can then be heated to reflux temperature for a period of from about Vi to about 2 hours. The desired product can then be collected by filtration if it is precipitated, or by evaporation of the organic solvent if it is soluble in it.

Examples of suitable compounds of the formula VT for the preparation of the new compounds are the following compounds:

so the dimethylacetal of 2-methylaminoacetaldehyde, the dimethylacetal of 2-ethylaminoacetaldehyde, the dimethylacetal of 2-propylaminoacetaldehyde, the dimethylacetal of 2-allylaminoacetaldehyde, the dimethylacetal of 2-chloromethyI-aminoalethylacetaldehyde dimethyl acetaldehyde of 2-propargylaminoacetaldehyde and the like.

Typical examples of suitable compounds of the general formula VII for the preparation of the new compounds are the following compounds: 6o 2-aminobenzothiazole, 2-amino-5-methylbenzothiazole, 2-amino-6-chlorobenzothiazole, 2-amino-4,5-dimethylbenzo- thiazole, 2-amino-7-bromobenzothiazole, 2-amino-6-methoxy-benzothiazole, 2-amino-6-fluorobenzothiazole, 2-amino-4-methyl-6-chlorobenzothiazole, 2-amino-4-chloromethylbenzothia- 65 zol, 2-amino-5-bromoethylbenzothiazole, 2-amino-6-trifluoromethylbenzothiazole and the like.

Typical examples of compounds of the formulas VIII and IX which are used to prepare the new compounds

9

633411

are the acid chlorides or anhydrides of the following acids:

Acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, octanoic acid, dodecanoic acid, octadecanoic acid, acrylic acid, butenic acid, pentenoic acid, chloroacetic acid, bromoacetic acid, ß-chlorobutanoic acid, cyclohexylcarbonic acid, cyclopropylearbonic acid, benzoic acid, toluic acid, 4-chlorobenzoic acid, 4-chlorobenzoic acid, 4-chlorobenzoic acid Fluorobenzoic acid, 4-methoxybenzoic acid, 4-ethoxybenzoic acid, 4-chloromethylbenzoic acid, 4-trifluoromethylbenzoic acid, 3,4,5-trichlorobenzoic acid, 3-methylthiobenzoic acid, 3-ethylthiobenzoic acid, 4-butylthiobenzoic acid, phenylacetic acid, phenylacetic acid, phenylacetic acid, Butynic acid, methoxyacetic acid, ß-methoxypropionic acid, y-ethoxy-butanoic acid and the like.

The processes for the preparation of the new compounds are explained in more detail using the examples.

Preparation 1

Preparation of benzothiazol-2-yl isocyanate dimer. A saturated solution of phosgene in ethyl acetate (1200 ml) is placed in a glass reaction vessel equipped with a mechanical stirrer, a thermometer and a reflux condenser. 100.0 g of 2-aminobenzothiazole (0.67 mol) is then added with stirring. After the addition is complete, the reaction mixture is warmed and held under reflux conditions for about an hour. The reaction mixture is then evaporated to dryness, giving the desired product, namely the isocyanate dimer of benzothiazol-2-yl, in the form of a yellow solid which has a melting point of 250-252 ° C.

Preparation 2

Preparation of the dimethylacetal of 2- (l-methyl-3-benzothiazol-2-ylureid) acetaldehyde The isocyanate dimer of benzothiazol-2-yl, which was prepared in preparation 1, 300 ml of benzene and the dimethylacetal of 2-methylaminoacetaldehyde (80 g; 0.67 mol) are placed in a glass reaction container equipped with a mechanical stirrer and a thermometer. The reaction mixture is stirred at room temperature for a period of about one hour. After this time, the mixture is filtered to remove a yellow solid that has formed. The filtrate is then freed from the solvent under reduced pressure and the desired product is obtained, namely the dimethyl acetal of 2- (l-methyl-3-benzothiazol-2-ylureid) acetaldehyde in the form of an oil.

example 1

Preparation of l-benzothiazol-2-yl-3-methyl-5-hydroxy-l, 3-imidazolidin-2-one The dimethyl acetal of 2- (l-methyl-3-benzothiazol-2-ylureid) acetaldehyde (150 g ), 750 ml of methanol, 750 ml of water and 75 ml of concentrated hydrochloric acid are placed in a glass reaction container which is equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture is kept under a protective gas atmosphere made of nitrogen and the mixture is heated to the reflux temperature over a period of about 15 minutes. After this time the mixture is freed from the solvent and the residue is mixed with aqueous sodium bicarbonate solution (500 ml). The mixture is then extracted with ethyl acetate and the solution thus obtained is dried over anhydrous magnesium sulfate. The dried solution is then freed from the solvent, whereby the desired product, namely l-benzothiazol-2-yl-3-methyl-5-hydroxy-l, 3-imidazolidin-2-one, is obtained in the form of a yellow solid which is one Has melting point of 168 to 170 ° C.

Example 2

Preparation of l-benzothiazol-2-yl-3-methyl-5-ethiamino-1,3-imidazolidin-2-one 0.1 mol of l-benzothiazol-2-yl-3-methyl-5-hydroxy-1,3 -imidazolidin-2-one and 100 ml of heptane are placed in a glass reaction container which is equipped with a mechanical stirrer, a thermometer, a Dean-Stark water separator and a reflux condenser. 0.1 mole of ethylamine is placed in the reaction vessel and the mixture is heated to reflux conditions and the water that forms is removed. When no more water is released, the reaction mixture is freed from the solvent under reduced pressure to give the desired product, namely l-benzothiazol-2-yl-3-methyl-5-ethylamino-1,3-imidazolidin-2 -on receives.

Example 3

Preparation of l-benzothiazol-2-yl-3-methyl-5-acetyloxy-1,3-imidazolidin-2-one 0.1 mol of l-benzothiazol-2-yl-3-methyl-5-hydroxy-1,3 -imidazolidin-2-one, 0.11 mol acetyl chloride and 0.11 mol pyridine are introduced into a glass reaction vessel which is equipped with a mechanical stirrer and a thermometer. The reaction mixture is stirred for a period of about 15 minutes and then allowed to stand for a period of about 2 hours. 100 ml of water and 30 ml of hexane are then added to the mixture. The organic phase is then separated from the aqueous phase and dried over anhydrous magnesium sulfate. The dried solution is then filtered and the solvent is removed under reduced pressure to give the desired product, 1-benzothiazol-2-yl-3-methyl-5-acetyloxy-1,3-imidazoli-din-2-one, as a residue receives.

Preparation 3

Preparation of the 5-methylbenzothiazol-2-yl isocyanate dimer A saturated solution of phosgene in ethyl acetate (200 ml) is placed in a glass reaction vessel equipped with a mechanical stirrer, a thermometer and a reflux condenser. 0.1 mol of 2-amino-5-methylbenzothiazole are added with stirring. After the addition is complete, the reaction mixture is heated to reflux for a period of about one hour. After this time the mixture is cooled and the solid products that have formed are recovered by filtration. The solid is dried to give the desired product, namely 5-methylbenzothiazol-2-yl isocyanate dimer.

Preparation 4

Preparation of the dimethyl acetal of 2- [l-methyl-3-

(5-methylbenzothiazol-2-yl) ureid] acetaldehyde 5-methylbenzothiazol-2-yl isocyanate dimers (0.1 mol), the dimethyl acetal of 2-methylaminoacetaldehyde (0.2 mol) and 100 ml of benzene are placed in a glass reaction container, which is equipped with a mechanical stirrer and a thermometer. The reaction mixture is at room temperature for a period of

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633 411

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stirred for about an hour. The reaction mixture is then filtered and the filtrate is freed from the solvent, whereby the desired product, namely the dimethyl acetal of 2- [l-methyl-3- (5-methyl-benzothiazol-2-yl) ureid] acetaldehyde, is obtained as a residue.

Example 4

Preparation of 1- (5-methylbenzothiazol-2-yl) -3-methyl-5-hydroxy-1,3-imidazolidin-2-one 15 g of the dimethyl acetal of 2- [l-methyl-3- (5-methyl- benzothiazol-2-yl) ureid] acetaldehyde, 200 ml of water, 200 ml of methanol and 10 ml of concentrated hydrochloric acid are introduced into a glass reaction vessel which is equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture is heated to reflux temperature over a period of about 15 minutes. The reaction mixture is then freed from the solvent under reduced pressure and a residue remains. This residue is recrystallized, giving the desired product, namely 1- (5-methylbenzothiazol-2-yl) -3-methyl-5-hydroxy-1,3-imidazolidin-2-one.

Example 5

Preparation of 1- (5-methylbenzothiazol-2-yl) -3-methyl-5-t-butylamino-1,3-imidazolidin-2-one 0.1 mol of 1- (5-methylbenzothiazol-2-yl) -3 -methyl-5-hydroxy-l, 3-imidazolidin-2-one and 100 ml of heptane are placed in a glass reaction container which is equipped with a mechanical stirrer, a thermometer and a Dean-Stark water separator and a reflux condenser, brought in. 0.1 mol of t-butylamine is introduced into the reaction vessel and the mixture is heated to the reflux temperature, and the water formed in the reaction is removed. After no more water has been separated off, the reaction mixture is freed from the solvent under reduced pressure, whereby the desired product, namely 1- (5-methylbenzothiazol-2-yl) -3-methyl-5-t-butylamino-l, 3- imidazolidin-2-one obtained as residue.

Example 6

Preparation of 1- (5-methylbenzothiazol-2-yl) -3-methyl-5-acryloyloxy-1,3-imidazolidin-2-one 0.1 mol of 1- (5-methylbenzothiazol-2-yl) -3-methyl -5-hy-hydroxy-l, 3-imidazolidin-2-one, 0.11 mol of acrylic acid chloride and 0.11 mol of pyridine are introduced into a glass reaction container which is equipped with a mechanical stirrer and a thermometer. The reaction mixture is stirred for a period of about 15 minutes and then allowed to stand for a period of about 2 hours. 100 ml of water and 30 ml of hexane are then added to the solution. The organic phase is then separated from the aqueous phase and dried over anhydrous magnesium sulfate. The dried solution is then filtered and the solvent is removed under reduced pressure, giving the desired compound, namely 1- (5-methylbenzothiazol-2-yl) -3-methyl-5-acryloyloxy-1,3-imidazolidin-2-one received as a backlog.

Preparation 5 Preparation of 6-chlorobenzothiazol-2-yl isocyanate dimer A saturated solution of phosgene in 200 ml of ethyl acetate is introduced into a glass reaction vessel which is equipped with a mechanical stirrer, a thermometer and a reflux condenser. 2-Amino-6-chlorobenzothiazole (0.1 mol) is added with stirring. After the addition is complete, the reaction mixture is heated to reflux temperature for about an hour. After this period has elapsed, the mixture is cooled and the solid that has formed is recovered by filtration. The solid is dried and the product 6-chlorobenzothiazol-2-yl isocyanate dimer is obtained.

Preparation 6

Preparation of the dimethylacetal of 2- [l-allyl-3- (6-chlorobenzothiazol-2-yl) ureide] acetaldehyde 0.1 mol of 6-chlorobenzothiazol-2-yl isocyanate dimers, 0.2 mol of the dimethylacetal of 2-allylaminoacetaldehyde and 100 ml of benzene are placed in a glass reaction container equipped with a mechanical stirrer and a thermometer. The reaction mixture is stirred at room temperature for a period of about one hour. The reaction mixture is then filtered and the filtrate is freed from the solvent and the desired product, namely the dimethyl acetal of 2- [l-allyl-3- (6-chlorobenzothiazol-2-yl) -ureid] acetaldehyde, is obtained as a residue.

Example 7

Preparation of l- (6-chlorobenzothiazol-2-yl) -3-allyl-

5-hydroxy-l, 3-imidazolidin-2-one 15 g of the dimethyl acetal of 2- [l-allyl-3- (6-chlorobenzothiazol-2-yl) ureid] acetaldehyde, 200 ml of water, 200 ml of methanol and 10 ml Concentrated hydrochloric acid is placed in a glass reaction vessel equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture is heated to reflux temperature over a period of about 15 minutes. After this time, the reaction mixture is freed from the solvent under reduced pressure, and a residue remains. This residue is recrystallized and the desired product is obtained, namely 1- (6-chlorobenzothiazol-2-yl) -3-allyl-5-hydroxy-1,3-imidazolidin-2-one.

Example 8

Preparation of l- (6-chlorobenzothiazol-2-yl) -3-allyl-

5-allylamino-l, 3-imidazolidin-2-one 0.1 mol l- (6-chlorobenzothiazol-2-yl) -3-allyl-5-hydroxy-1,3-imidazolidin-2-one and 100 ml heptane are placed in a glass reaction vessel equipped with a mechanical stirrer, a thermometer, a Dean-Stark water separator and a reflux condenser. 0.1 mol of allylamine is introduced into the reaction vessel and the mixture is heated to the reflux temperature while the water which forms is separated off. After no more water is formed, the reaction solution is freed from the solvent under reduced pressure, giving the desired product, namely 1- (6-chlorobenzothiazol-2-yl) -3-allyl-5-allylamino-1,3-imidazolidine Receives -2-one as residue.

Example 9

Preparation of l- (6-chlorobenzothiazol-2-yl) -3-allyl-

5-a-chloroacetyloxy-l, 3-imidazolidin-2-one 0.1 mol l- (6-chlorobenzothiazol-2-yl) -3-allyl-5-hydroxy-l, 3-imidazolidin-2-one, 0 , 11 moles of a-chloroacetyl chloride and 0.11 moles of pyridine are placed in a glass reaction container equipped with a mechanical stirrer and a thermometer. The reaction mi5

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633 411

The mixture is stirred for a period of about 15 minutes and then left to stand for about 2 hours. 100 ml of water and 30 ml of hexane are then added to the mixture. The organic phase is then separated from the aqueous phase and dried over anhydrous magnesium sulfate. The dried solution is filtered and the solvent is removed under reduced pressure, giving the desired product, namely 1- (6-chlorobenzothiazol-2-yl) -3-allyl-5-a-chloroacetyloxy-1,3-imidazolidin-2- one receives as a backlog.

Preparation 7 Preparation of 7-bromobenzothiazol-2-yl isocyanate dimer A saturated solution of phosgene in 200 ml of ethyl acetate is introduced into a glass reaction vessel which is equipped with a mechanical stirrer, a thermometer and a reflux condenser. 2-Amino-7-bromobenzothiazole (0.1 mol) is added with stirring. The mixture is then cooled and the solid product that forms is recovered by filtration. The solid is then dried and the desired product is obtained, namely 7-bromobenzothiazol-2-yl isocyanate dimers.

Preparation 8

Preparation of the dimethyl acetal of 2- [l-propargyl

3- (7-bromobenzothiazol-2-yl) ureid] acetaldehyde 0.1 mol of 7-bromobenzothiazol-2-yl isocyanate dimers, 0.2 mol of dimethylacetal of 2-propargylaminoacetaldehyde and 100 ml of benzene are placed in a glass reaction container which is filled with a mechanical stirrer and a thermometer. The reaction mixture is stirred at room temperature for a period of about one hour. The reaction mixture is then filtered and the filtrate is freed from the solvent, whereby the desired product, namely the dimethyl acetal of 2- [l-propargyl-3- (7-bromobenzothiazol-2-yl) ureid] acetaldehyde, is obtained as a residue.

Example 10

Preparation of l- (7-bromobenzothiazol-2-yl) -3-propargyl-5-hydroxy-1,3-imidazolidin-2-one 15 g of the dimethyl acetal of 2- [l-propargyl-3- (7-bromo- benzothiazol-2-yl) ureid] acetaldehyde, 200 ml of water, 200 ml of methanol and 10 ml of concentrated hydrochloric acid are introduced into a glass reaction container which is equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture is heated to reflux temperature over a period of 15 minutes. The reaction mixture is then freed from the solvent under reduced pressure and a residue remains. This residue is recrystallized, whereby the desired product, namely the I- (7-bromobenzothiazol-2-yl) -3-propargyl-5-hydroxy-l, 3-imidazolidin-2-one, is obtained.

Example 11

Preparation of l- (7-bromobenzothiazol-2-yl) -3-propargyl-5-ß-chloroethylamino-l, 3-imidazolidin-2-one 0.1 mol l- (7-bromobenzothiazol-2-yl) -3 -propargyl-5-hydroxy-l, 3-imidazolidin-2-one and 100 ml of heptane are placed in a glass reaction container equipped with a mechanical stirrer, a thermometer, a Dean-Stark water separator and a reflux condenser. 0.1 mol of ß-chloroethylamine is introduced into the reaction vessel and the mixture is heated to reflux temperature while the resulting

Water collects in the separator. After no more water has been separated off, the reaction mixture is freed from the solvent under reduced pressure, whereby the desired product, namely 1- (7-bromobenzothiazol-2-yl) -3-propargyl-5-β-chloroethylamino-1,3- imidazolidin-2-one obtained as residue.

Example 12

Preparation of l- (7-bromobenzothiazol-2-yl) -3-propargyl-5-propinoyloxy-1,3-imidazolidin-2-one 0.1 mol of l- (7-bromobenzothiazol-2-yl) -3-propargyl -5-hy-hydroxy-l, 3-imidazolidin-2-one, 0.11 mol of propinoyl chloride and 0.11 mol of pyridine are introduced into a glass reaction container equipped with a mechanical stirrer and a thermometer. The reaction mixture is stirred for about 15 minutes and then allowed to stand for 2 hours. 100 ml of water and 30 ml of hexane are then added to the mixture. The organic phase is then separated from the aqueous phase and dried over anhydrous magnesium sulfate. The dried solution is then filtered and the solvent is removed under reduced pressure, giving the desired product, namely 1 - (7-bromobenzothiazol-2-yl) -3-propargyl-5-propinoyloxy-l, 3-imidazolidin-2-one received as a backlog.

Preparation 9

Preparation of 4-methoxybenzothiazol-2-yl isocyanate dimer A saturated solution of phosgene in 200 ml of ethyl acetate is placed in a glass reaction vessel equipped with a mechanical stirrer, a thermometer and a reflux condenser. 0.1 mol of 2-amino-4-methoxybenzothiazole are added with stirring. After the addition is complete, the reaction mixture is heated to reflux for a period of about one hour. The mixture is then cooled and the solid formed is collected by filtration. The solid is dried to give the desired product, namely 4-methoxy-benzothiazol-2-yl isocyanate dimers.

Preparation 10

Preparation of the dimethyl acetal of 2- [l-ethyl-3-

(4-methoxybenzothiazol-2-yl) ureid] acetaldehyde 0.1 mol of 4-methoxybenzothiazol-2-yl isocyanate dimers, 0.2 mol of dimethylacetal of 2-ethylaminoacetaldehyde and 100 ml of benzene are placed in a glass reaction container that is equipped with a mechanical stirrer and equipped with a thermometer. The reaction mixture is stirred at room temperature for a period of about one hour. The reaction mixture is then filtered and the filtrate is freed from the solvent, whereby the desired product, namely the dimethylacetal of 2- [l-ethyl-3- (4-methoxybenzothiazol-2-yl) ureid] acetaldehyde, is obtained as a residue.

Example 13

Preparation of l- (4-methoxybenzothiazol-2-yl) -3-

ethyl-5-hydroxy-1,3-imidazolidin-2-one 15 g of the dimethyl acetal of 2- [l-ethyl-3- (4-methoxybenzothiazol-2-yl) ureid] acetaldehyde, 200 ml of water, 200 ml of methanol and 10 ml of concentrated hydrochloric acid are placed in a glass reaction container equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture is heated to reflux temperature over a period of about 15 minutes. Subsequently

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633 411

12th

the reaction mixture is freed from the solvents under reduced pressure and a residue remains. This residue is recrystallized and the desired product is obtained, namely 1- (4-methoxybenzothiazol-2-yl) -3-ethyl-5-hydroxy-1,3-imidazolidin-2-one.

Example 14

Preparation of l- (4-methoxybenzothiazol-2-yl) -3-ethyl-5-ß-hydroxyethylamino-1,3-imidazolidin-2-one 0.1 mol of l- (4-methoxybenzothiazoI-2-yl) -3 Ethyl-5-hydroxy-l, 3-imidazolidin-2-one and 100 ml of heptane are placed in a glass reaction container equipped with a mechanical stirrer, a thermometer, a Dean-Stark water separator and a reflux condenser is introduced. 0.1 mol of β-hydroxyethylamine are introduced into the reaction vessel and the mixture is heated to the reflux temperature while the water which forms is separated off. When water is no longer separated, the reaction mixture is freed from solvents under reduced pressure, giving the desired product, namely 1- (4-methoxybenzothiazol-2-yl) -3-ethyl-5-β-hydroxyethylamino-1,3- imidazolidin-2-one obtained as residue.

Example 15

Preparation of l- (4-methoxybenzothiazol-2-yl) -3-ethyl-5-a-methoxyacetyloxy-1,3-imidazolidin-2-one 0.1 mol of l- (4-methoxybenzothiazol-2-yl) -3 -ethyl-5-hy-hydroxy-l, 3-imidazolidin-2-one, 0.11 mol of a-methoxyacetyl chloride and 0.11 mol of pyridine are placed in a glass reaction container equipped with a mechanical stirrer and a thermometer is introduced. The reaction mixture is stirred for a period of about 15 minutes, then allowed to stand for about 2 hours. 100 ml of water and 30 ml of hexane are then added to the mixture. The organic phase is then separated from the aqueous phase and dried over anhydrous magnesium sulfate. The dried solution is then filtered and the solvent is removed under reduced pressure, giving the desired product, namely 1- (4-methoxybenzothiazol-2-yl) -3-ethyl-5-a-methoxyacetyloxy-1,3-imidazolidin-2 -one received as a backlog.

Preparation 11 Preparation of 5-fluorobenzothiazol-2-yl isocyanate dimer A saturated solution of phosgene in 200 ml of ethyl acetate is introduced into a glass reaction container which is equipped with a mechanical stirrer, a thermometer and a reflux condenser. 0.1 mol of 2-amino-5-fluorobenzothiazole are added with stirring. After the addition is complete, the reaction mixture is heated to reflux temperature for one hour. After this time the reaction mixture is cooled and the solid formed is removed by filtration. The solid is then dried to give the desired product, 5-fluorobenzothiazol-2-yl isocyanate dimers.

Preparation 12

Preparation of the dimethyl acetal of 2- [l-chloromethyl-3- (5-fluorobenzothiazol-2-yl) ureide] acetaldehyde 0.1 mol of 5-fluorobenzothiazol-2-yl isocyanate dimer, 0.2 mol of dimethyl acetal of 2-chloromethylaminoacetaldehyde and 100 ml Benzene is placed in a glass reaction container equipped with a mechanical stirrer and a thermometer. The reaction mixture is stirred at room temperature for a period of about one hour. After this time the reaction mixture is filtered and the filtrate is freed from the solvent, whereby the desired product, namely the dimethyl acetal of 2- [l-chloromethyl-3- (5-fluoro-benzothiazol-2-yl) ureid] acetaldehyde, is left as a residue receives.

Example 16

Preparation of l- (5-fluorobenzothiazol-2-yl) -3-ehlormethyl-5-hydroxy-1,3-imidazolidin-2-one The dimethyl acetal of 2- [l-chloromethyl-3- (5-fluorobenzothiazol- 2-yl) ureid] acetaldehyde (15 g), 200 ml of water, 200 ml of methanol and 10 ml of concentrated hydrochloric acid are introduced into a glass reaction container equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture is heated to reflux temperature over a period of about 15 minutes. The reaction mixture is then freed from the solvent under reduced pressure and a residue remains. This residue is recrystallized, whereby the desired product, namely 1- (5-fluorobenzothiazol-2-yl) -3-chloromethyl-5-hydroxy-1,3-imidazolidin-2-one, is obtained.

Example 17

Preparation of l- (5-fluorobenzothiazol-2-yl) -3-chlorme-

thyl

5-methoxymethylamino-l, 3-imidazolidin-2-one 0.1 mol l- (5-fluorobenzothiazol-2-yl) -3-chloromethyl-5-hydroxy-l, 3-imidazolidin-2-one and 100 ml heptane are placed in a glass reaction vessel equipped with a mechanical stirrer, a thermometer, a Dean Stark water separator and a reflux condenser. 0.1 mole of methoxymethylamine is added to the reaction vessel and the mixture is heated to reflux temperature while separating the water that forms. After water is no longer released, the reaction mixture is freed from the solvent under reduced pressure, whereby the desired product, namely 1- (5-fluorobenzothi-azol-2-yl) -3-chloromethyl-5-methoxymethylamino-1,3- imida-zolidin-2-one obtained as a residue.

Example 18

Preparation of l- (5-fluorobenzothiazol-2-yl) -3-chloromethyl-5-cyclopropylcarbonyloxy-l, 3-imidazolidin-2-one 0.1 mol l- (5-fluorobenzothiazol-2-yl) -3 -chloromethyl-5-hydroxy-l, 3-imidazolidin-2-one, 0.11 mol of cyclopropylcarbonyl chloride and 0.11 mol of pyridine are introduced into a glass reaction container which is equipped with a mechanical stirrer and a thermometer . The reaction mixture is stirred for a period of about 15 minutes and then left to stand for about 2 hours. 100 ml of water and 30 ml of hexane are then added to the mixture. The organic phase is then separated from the aqueous phase and dried over anhydrous magnesium sulfate. The dried solution is then filtered and the solvent is removed under reduced pressure to give the desired product, namely 1- (5-fluorobenzothiazol-2-yl) -3-chloromethyl-5-cyclopropylcarbonyloxy-l, 3-imidazolidin-2 -one received as a backlog.

Preparation 13

Preparation of 5-trifluoromethylbenzothiazol-2-yl isocyanate dimer A saturated solution of phosgene in 200 ml of ethyl acetate is placed in a glass reaction container which

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13

633411

equipped with a mechanical stirrer, a thermometer and a reflux condenser. 0.1 mol of 2-amino-5-trifluoromethylbenzothiazole are added with stirring. After the addition is complete, the reaction mixture is heated to reflux temperature for one hour. The mixture is then cooled and the solid formed is collected by filtration. The solid is then dried to give the desired product, 5-trifluoromethylbenzothiazol-2-yl isocyanate dimers.

Preparation 14

Preparation of the dimethyl acetal of 2- [l-β-bromoethyl-3- (5-trifluoromethylbenzothiazol-2-yl) ureid] acetaldehyde 0.1 mol of 5-trifluoromethylbenzothiazol-2-yl isocyanate dimers, 0.2 mol of dimethyl acetal of 2-β- Bromoethylamino-acetaldehyde and 100 ml of benzene are placed in a glass reaction container equipped with a mechanical stirrer and a thermometer. The reaction mixture is stirred at room temperature for a period of about one hour. The reaction mixture is then filtered and the filtrate is freed from the solvent, whereby the desired product, namely the dimethyl acetal of 2- [l-β-bromoethyl-3- (5-trifluoromethylbenzothiazol-2-yl) ureide] acetaldehyde, is obtained as a residue.

Example 19

Preparation of 1- (5-trifluoromethylbenzothiazol-2-yl) -

3-ß-bromoethyl-5-hydroxy-l, 3-imidazolidin-2-one 15 g of dimethyl acetal of 2- [l-ß-bromoethyl-3- (5-trifluoromethylbenzothiazol-2-yl) ureide] acetaldehyde, 200 ml of water, 200 ml of methanol and 10 ml of concentrated hydrochloric acid are introduced into a glass reaction container which is equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture is heated to reflux temperature for about 15 minutes. The reaction mixture is then freed from the solvent under reduced pressure, a residue remaining. This residue is recrystallized, whereby the desired product, namely 1- (5-trifluoromethylbenzothiazol-2-yl) -3-β-bromoethyl-5-hydroxy-1,3-imidazolidin-2-one, is obtained.

Example 20

Preparation of l- (5-trifluoromethylbenzothiazol-2-yl) -3-ß-bromoethyl-5-cyelopropylamino-l, 3-imidazolidin-2-one 0.1 mol l- (5-trifluoromethylbenzothiazol-2-yl) -3 -ß-bromo-ethyl-5-hydroxy-l, 3-imidazolidin-2-one and 100 ml of heptane are placed in a glass reaction vessel equipped with a mechanical stirrer, a thermometer and a Dean-Stark water separator and a reflux condenser is introduced. 0.1 mol of cyclo-propylamine is introduced into the reaction vessel and the mixture is heated to reflux temperature while the water which forms is separated off. After no more water has been developed, the reaction mixture is freed from the solvent under reduced pressure, whereby the desired product, namely 1- (5-trifluoromethylbenzothiazol-2-yl) -3-β-bromoethyl-5-cyclop-ropylamino-1, 3-imidazolidin-2-one receives.

Example 21

Preparation of l- (5-trifluoromethylbenzothiazol-2-yl) -3-ß-bromoethyl-5-benzoyloxy-1,3-imidazolidin-2-one 0.1 mol l- (5-trifluoromethylbenzothiazol-2-yl) -3 -ß-bromo-ethyl-5-hydroxy-l, 3-imidazolidin-2-one, 0.11 mol of benzoyl chloride and 0.11 mol of pyridine are placed in a glass reaction container equipped with a mechanical stirrer and a thermometer is introduced. The reaction mixture is stirred for about 15 minutes and then left to stand for about 2 hours. 100 ml of water and 30 ml of hexane are then added to the mixture. The organic phase is then separated from the aqueous phase and dried over anhydrous magnesium sulfate. The dried solution is then filtered and the solvent is removed under reduced pressure, giving the desired product, namely 1 - (5-trifluoromethylbenzothiazol-2-yl) -3-β-bromo-ethyl-5-benzoyloxy-1,3-imidazolidine Receives -2-one as residue.

Example 22

Preparation of l-benzothiazol-2-yl-3-methyl-5-aniline-1,3-imidazolidin-2-one 0.1 mol of l-benzothiazol-2-yl-3-methyl-5-hydroxy-1,3 -imidazolidin-2-one and 100 ml of heptane are introduced into a glass reaction container which is equipped with a mechanical stirrer, a thermometer and a Dean-Stark water separator and a reflux condenser. 0.1 mol of aniline are introduced into the reaction vessel and the mixture is heated under reflux while the water which forms is separated off. After no more water is released, the reaction mixture is freed from the solvent under reduced pressure, whereby the desired product, namely 1-ben-zothiazol-2-yl-3-methyl-5-aniline-1,3-imidazolidin-2- one receives as a backlog.

Example 23

Preparation of l-benzothiazol-2-yl-3-methyl-5-dimethyl-amin-l, 3-imidazolidin-2-one 0.1 mol of l-benzothiazol-2-yl-3-methyl-5-hydroxy-l , 3-imidazolidin-2-one and 100 ml of heptane are placed in a glass reaction container equipped with a mechanical stirrer, a thermometer, a Dean-Stark water separator and a reflux condenser. 0.1 mol of dimethylamine is introduced into the reaction vessel and the mixture is heated to the reflux temperature while the water which forms is separated off. After water is no longer released, the reaction mixture is freed from the solvent under reduced pressure, whereby the desired product, namely l-benzothiazol-2-yl-3-methyl-5-dimethylamino-l, 3-imidazolidin-2- one receives as a backlog.

The new compounds are particularly valuable for weed control because they are toxic to many species and groups of weeds and are essentially non-toxic to crops. The exact amount of compound required depends on a variety of factors, including the resistance of the particular weed species, the weather, the type of substrate or soil, the form of application or application, the type of crop on the same area and the like . Accordingly, application of only up to about 7-14 mg of the active compound per square meter may be sufficient to properly control light weed infestation that occurs under poor growing conditions, while the application of 1 g or more of the active compound per square meter may be necessary to achieve a good control of a violent weed infestation with hardy or perennial weeds that grow under favorable conditions.

The herbicidal toxicity of the new compounds can be described well according to the following, according to the prior art

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633 411

14

known, test methods can be determined by performing application tests before and after infestation.

The herbicidal activity of the new compounds mentioned can be demonstrated by carrying out experiments which concern preventive control of a large number of weeds. In these experiments, small plastic greenhouse pots filled with dry soil are sown with various weed seeds. 24 hours or less after sowing, the pots are watered until the soil is wet and the test compound, which is in the form of an aqueous emulsion of an acetone solution containing emulsifiers, is sprayed onto the surface of the earth in the desired concentration.

After spraying, the soil containers are brought into the greenhouse and, if necessary, additional heating is carried out, depending on whether this is necessary, and watering is carried out daily or more frequently if necessary. The plants are kept under these conditions for a period of about 15 to 21 days, during which time the condition of the plants and the degree of their damage is recorded on a 10-point scale, which has the following ratings:

0 = no damage 1 and 2 = slight damage 3 and 4 = moderate damage 5 and 6 = moderate damage 7, 8 and 9 = severe damage and 10 = plant death The herbicidal activity of the new compounds can also be demonstrated by experiments to test the control of a variety of weeds after infestation. In these experiments, the compounds to be tested are formulated in the form of aqueous emulsions and sprayed onto the leaves of the weeds, which have reached a predetermined size, in the desired dosage. After spraying the plants, they are placed in a greenhouse and watered daily or more often. No water is applied to the leaves of the treated plants. The severity of the injury is assessed 10 to 15 days after treatment, using the same 10-point scale defined above.

Table I

Assessment of the intensity of damage caused by the product from Example 1:

Weed type Application amount in g / m2 (lbs / acre)

0.448 0.112 0.056 0.028 0.014

(4)

(1)

(0.5)

(0.25)

(0.125)

Cyperus

0

0

0

-

-

Wild oats

10th

7

7.5 *

0

0

Datura

(Datura stramonium)

.3

0

7 *

5

10th

Cissampelos pareira

10th

10th

10 *

10th

0

Chenopodium

10th

9

9.5

10th

8th

Wild mustard

10th

10th

10 *

10th

10th

Yellow foxtail

(Setaria lutescens)

3rd

2nd

5 *

7

7

Table I (continued)

Weed type Application amount in g / m2 (lbs / acre)

0.448 0.112 0.056 0.028 0.014 (4) (1) (0.5) (0.25) (0.125)

Echinochloor crus

galli P. Beauv

9

9

7 *

3rd

0

Digitarla

6

4th

2.5

0

0

Wheat-like grass

the group bromos

10th

10th

10 *

4th

0

Ipomea purpurea

10th

7

4.5 *

0

0

Fluminea festucacea

-

-

7

5

0

Winds

Convolvulus sepium

-

- ■

3rd

0

0

Sorghum halepense

-

-

4th

0

0

Quackgrass

-

-

10th

10th

5

* The values are mean values from two parallel tests.

The herbicidal activity of the compounds prepared by the process according to the invention is also shown by experiments which were carried out to control a large number of weed species after infestation. In these experiments, the product from Example 1 was formulated in an aqueous emulsion and sprayed in the specified dosage onto the leaves of the weeds, which would have reached a prescribed size. After spraying, the plants were moved to a greenhouse and watered daily or more often. No water was applied to the leaves of the treated plants. The degree of damage was determined 14 days after treatment based on the 10-point scale described above. The efficacy of this compound is confirmed by the data in Table II.

Tables

Intensity of damage of the product from Example 1 to different types of weeds:

Weed type Application amount in g / m2

0.448 (4)

(lbs / acre) 0.112

(1)

0.056 (0.5)

Yellow foxtail

10th

10th

10th

Wild mustard

10th

10th

10th

Sorghum halepense

8th

5

4th

Chenopodium

10th

10th

10th

Ipomea purpurea

10th

10th

10th

Crabgrass

10th

10th

5

Wild oats

10th

10th

10th

Winch (Convolvus sepium)

10th

8th

8th

Datura

10th

10th

10th

Echinochloor cras-galli;

P. Beauv.

10th

10th

10th

Cyperus

5

2nd

0

5

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55

S

Claims (28)

633411 1 3 - N - RJ wherein R2 and R3 independently of one another are a hydrogen atom, an alkyl group, an alkenyl group, a halogenated alkyl group, a hydroxyalkyl group, an alkoxyalkyl group, a cycloalkyl group or a group of the formula h (5-itl) 30th means, in this formula p = 0 or 1, m = 0 or an integer in the range from 1 to 3, and Y represents an alkyl group, an alkoxy group, an alkylthio group, a halogen atom, a halogenated alkyl group, a nitro group or a cyano group. (1) a hydroxyl group, 2. Herbicidal composition according to claim 1, characterized in that in the active ingredient of formula I contained in it X is an alkyl group with 1-6 carbon atoms optionally substituted with chlorine or bromine, a trifluoromethyl group, an alkoxy group with 1-6 carbon atoms, a chlorine atom or bromine atom, R1 is an optionally halogen-substituted alkyl group with 1-6 carbon atoms, an alkenyl group with up to 6 carbon atoms or a group of the formula: 35 - C - C: r- : CH 40 45 means what R4 and R5 independently of one another denote hydrogen atoms or alkyl groups with up to 3 carbon atoms, R2 and R3 independently of one another are hydrogen atoms, alkyl, haloalkyl, hydroxyalkyl or alkoxyalkyl groups each having 1 to 6 carbon atoms in the alkyl part, alkenyl groups having up to 6 carbon atoms, cycloalkyl groups having 3 to 7 carbon atoms or groups of the formula H (5-in) - (ci 2J P mean in which 60 p = 0 or 1, m = 0 or an integer in the range from 1 to 3, Y is an alkyl, alkoxy, alkylthio, chloroalkyl or bromoalkyl group each having 1 to 6 carbon atoms in the alkyl part, the trifluoromethyl group, a halogen atom, the nitro group or the cyano group, R6 is an alkyl, haloalkyl, hydroxyalkyl or alkoxyalkyl group each having 1 to 6 carbon atoms in the (2) an amine group of formula r2 2nd PATENT CLAIMS Î. Herbicidal agent, characterized in that it is a new 1-benzothiazolyl-imidazolidinone of formula I as active ingredient Q I ch- is what R6 is an alkyl group, an alkenyl group, a halogenated alkyl group, a hydroxyalkyl group, an alkynyl group, an alkoxyalkyl group, a cycloalkyl group or a group of the formula -ch. H 3. Process for the preparation of a new 1-benzothia-zolyl-imidazolidinone of the formula II qjj ch- n \ / c - n being in this formula X represents an alkyl group, a halogen atom, a halogenated alkyl group or an alkoxy group, 3rd 633 411 Alkyl part, an alkenyl group with up to 6 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms or a grouping of the formula H (5-m) - <CH2) p • Y m means where m, p and Y are defined above. (4-n) (Ib) being in this formula X represents an alkyl group, a halogen atom, a halogenated alkyl group or an alkoxy group, n is 0.1 or 2, 30 R1 an alkyl group, an alkenyl group, a halogenated alkyl group or a group of the formula: R * l l 35 - C - C = CH RS is, in this formula 40 R4 and R5 independently of one another represent hydrogen atoms or alkyl groups, and Q "is an ester group of the formula 0 45 (III) in which R2 and R3 have the same meaning as in formula Ia, converted to the compounds of formula la. 4th R ! _ - C - C = CH P.S is, in this formula R4 and R5 independently represent hydrogen atoms or alkyl groups, and Q 'is an amine group of the formula R2 (4-n) \ ch- , c - n -ch. n - rj (Ia) wherein X represents an alkyl group, a halogen atom, a halogenated alkyl group or an alkoxy group, \ / C II 0 n is 0.1 or 2, R1 is an alkyl group, an alkenyl group, a halogenated alkyl group or a group of the formula: 633 411 4. The method according to claim 3, characterized in that l-benzothiazol-2-yl-3-methyl-5-hydroxy-l, 3-imidazolidin-2-one is produced. (4-n) in which X, n and R1 have the same meaning as in formula II, cyclized to the compound of formula II. (4-n) \ / C. II o n - p. 5 633 411 represents a nitro group or a cyano group, characterized in that a compound of the formula IV is cyclized to the hydroxy compound of the formula II by the process according to claim 3, and this is then cycled with an acid of the formula V. R6-COOH (V) in which R® has the same meaning as in formula Ib, or a reactive functional derivative of this acid esterified to give the compounds of formula Ib. 5. The method according to claim 3, characterized in that l- (5-methylbenzothiazol-2-yl) -3-methyl-5-hydroxy-l, 3-imidazolidin-2-one is produced. 5 n is 0, 1 or 2 and R1 is an alkyl group, an alkenyl group, a halogenated alkyl group or a group of the formula ch2 j-r1 - c - c: L r3 : ch is being in this formula (5 m) \ H 6. The method according to claim 3, characterized in that l- (6-chlorobenzothiazol-2-yl) -3-allyl-5-hydroxy-1,3-imidazolidin-2-one is produced. 7. The method according to claim 3, characterized in that l- (7-bromobenzothiazol-2-yl) -3-pro-pargyl-5-hydroxy-l, 3-imidazolidin-2-one is produced. Hi n- och - c - n - ch-, - ch II 0 (IV) och- 8. The method according to claim 3, characterized in that l- (4-methoxybenzothiazol-2-yl) -3-ethyl 40 5-hydroxy-1,3-imidazolidin-2-one produces. 9. The method according to claim 3, characterized in that l- (5-fluorobenzothiazol-2-yl) -3-chloromethyl-5-hydroxy-1,3-imidazolidin-2-one is produced. 45 10. The method according to claim 3, characterized in that l- (5-trifluoromethylbenzothiazol-2-yl) -3-ß-bromoethyl-5-hydroxy-1,3-imidazolidin-2-one is produced. 10th 10th - (ch2) ci) contains what X represents an alkyl group, a halogen atom, a halogenated alkyl group or an alkoxy group, 20 n is 0.1 or 2, R1 is an alkyl group, an alkenyl group, a halogenated alkyl group or a group of the formula: R - C - c- : ch - (ch2) mean, where p = 0 or 1, m = 0 or an integer in the range from 1 to 3, and Y represents an alkyl group, an alkoxy group, an alkylthio group, a halogen atom, a halogenated alkyl group, a nitro group or a cyano group, or (3) an ester group of the formula: O II s - 0 - C - R6 11. Process for the preparation of the new 1-benzothia-zolyl-imidazolidinone of formula Ia 50 Qx H 12. The method according to claim 11, characterized in that l-benzothiazol-2-yl-3-methyl-5-ethyl-amino-1,3-imidazolidin-2-one is produced. 13. The method according to claim 11, characterized in that l- (5-methylbenzothiazol-2-yl) -3-methyl-5-t-butylamino-l, 3-imidazolidin-2-one is produced. 14. The method according to claim 11, characterized in that l- (6-chlorobenzothiazol-2-yl) -3-allyl-5-allylamino-1,3-imidazolidin-2-one is produced. 15. The method according to claim 11, characterized in that l- (7-bromobenzothiazol-2-yl) -3-pro-pargyl-5-ß-chloroethylamino-l, 3-imidazolidin-2-one is produced. 16. The method according to claim 11, characterized in that l- (4-methoxybenzothiazol-2-yl) -3-ethyl-5-ß-hydroxyäthyIamino-l, 3-imidazolidin-2-one is produced. - 0 - C - R represents what R6 is an alkyl group, an alkenyl group, a halogenated alkyl group, a hydroxyalkyl group, an alkynyl group, an alkoxyalkyl group, a cycloalkyl group or a group of the formula 60 - (CH2) p, where in this formula p = 0 or list, 65 m = 0 or an integer in the range from 1 to 3, and Y is an alkyl group, an alkoxy group, an alkylthio group, a halogen atom, a halogenated alkyl group, 17. The method according to claim 11, characterized in that l- (5-fluorobenzothiazol-2-yl) -3-chloromethyl-5-methoxymethylamino-l, 3-imidazolidin-2-one is produced. 18. The method according to claim 11, characterized in that l- (5-trifluoromethylbenzothiazol-2-yl) -3-ß-bromoethyl-5-cyclopropylamino-l, 3-imidazolidin-2-one is produced. 19. The method according to claim 11, characterized in that l-benzothiazol-2-yl-3-methyl-5-anilino-1,3-imidazolidin-2-one is produced. 20. Process for the preparation of new 1-benzothia-zolyl-imidazolidinones of the formula Ib Q " - NO means what R2 and R3 independently of one another are a hydrogen atom, an alkyl group, an alkenyl group, a halogenated alkyl group, a hydroxyalkyl group, an alkoxyalkyl group, a cycloalkyl group or a group of the formula ! ck2) p, where p = 0 or 1, m = 0 or an integer in the range from 1 to 3, and Y represents an alkyl group, an alkoxy group, an alkylthio group, a halogen atom, a halogenated alkyl group, a nitro group or a cyano group, characterized in that a compound of the formula IV is cyclized to a corresponding hydroxy compound of the formula II by the process according to claim 3, and this then with ammonia or an amine of the formula III R H - N - R " ch ch- : c - n \ / C. number 1 20th H (4-n) V no (ii) R4 and R5 independently of one another represent hydrogen atoms or alkyl groups, characterized by having a connection of For-25 with IV: C - 21. The method according to claim 20, characterized in that l-benzothiazol-2-yl-3-methyl-5-acetyl-oxy-1,3-imidazolidin-2-one is produced. 22. The method according to claim 20, characterized in that l- (5-methylbenzothiazol-2-yl) -3-methyl-5-acryloyloxy-l, 3-imidazolidin-2-one is produced. 23. The method according to claim 20, characterized in that l- (6-chlorobenzothiazol-2-yl) -3-allyl-5-a-chloroacetyloxy-l, 3-imidazolidin-2-one is produced. 24. The method according to claim 20, characterized in that 5- that l- (7-bromobenzothiazol-2-yl) -3-pro- pargyl-5-propinoyloxy-l, 3-imidazolidin-2-one. 25. The method according to claim 20, characterized in that l- (4-methoxybenzothiazol-2-yl) -3-ethyl-5-a-methoxyacetyloxy-l, 3-imidazolidin-2-one is produced. io 26. The method according to claim 20, characterized in that l- (5-fluorobenzothiazol-2-yl) -3-chloromethyl-5-cyclopropylcarbonyloxy-l, 3-imidazolidin-2-one is produced. 25th 25th RS is, in this formula R4 and R5 independently of one another represent hydrogen atoms or alkyl groups, and Q has the following meanings: 27. The method according to claim 20, characterized in that 15- characterized in that l- (5-trifluoromethyl-benzothiazol-2-yl) -3- ß-Bromäthyl-5-benzoyloxy-l, 3-imidazolidin-2-one produces. 28. The method according to claim 20, characterized in that l-benzothiazol-2-yl-3-methyl-5-benzoyl-oxy-1,3-imidazolidin-2-one is produced.