DE2908254A1 - NEW PYRROLIDIN-2-ON DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, AND THE HERBICIDE COMPOSITIONS CONTAINING THEM - Google Patents

Description

ph 478 7908254

10 / We

PHIlAGRO, Lyon / France

Heue Pyrrolidin-2-one-Derivate _s Process for their preparation ^ and herbicidal compositions containing them

The invention relates to new pyrrolidin-2-one derivatives, their production, and the herbicidal compositions containing them.

The compounds according to the invention correspond to the general ones lOjem el

Ar

in which the individual symbols have the following meanings: Ar denotes a phenyl radical which is optionally substituted by 1 to 2 Substituents, which are identical or different from one another, can be substituted, selected from the halogen atoms, the alkyl radicals with 1 to 4 carbon atoms, the alkoxy radicals with 1 to 4 carbon atoms, the JLLkenyloxyl radicals with 2 to 4 carbon atoms, the .Alkinyloxylresten with 2 to 4 carbon atoms, Hydroxyl, nitro, iDrifluoromethyl, monoalkylcarb-

903334/0557

Amoyl with 1 Ms 4 carbon atoms in the alkyl partjdialkylcarbamojrl, in which each of the alkyte parts, pluralities identical or different from one another, comprises 1 Ms 4 carbon atoms, aliphatic acylamino with 2 Ms 5 carbon atoms or an Ar'-O radical, in which Ar ^{1 is} optionally substituted . Phenyl radical or a heterocyclic radical with 6 chain members which is optionally substituted and contains an oxygen, sulfur or nitrogen atom as a hetero atom; Ar can also denote an optionally substituted aromatic heterocyclic radical with 5 "to 6 chain members which contains 1 to 2 identical or different atoms selected from nitrogen, oxygen or sulfur atoms as heteroatoms.

R .. denotes an alkyl radical with 1 to 4 carbon atoms, a Cftcloalkylrest with 3 to 6 carbon atoms or an optionally substituted phenyl radical;
R ₂ denotes a hydrogen atom or the methyl radical.

The invention relates in particular to the 1-benzy-pyrrolidin-2-one derivatives "the lOrmel

in which the individual symbols have the following meanings:

Y is an atom or a radical selected from halogen and alkyl radicals with 1 to 4 carbon atoms, alkoxy groups with 1 to 4

Carbon atoms and the i-erifluoromethyl radical,

η is an integer equal to 1 or 2 with the proviso that, if η = 2, the substituents Y. are identical or different

could be,

R ₁ "means an alkyl radical having 1 to 3 carbon atoms or

the phenyl radical,

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Ep asked the meaning given for Pormel (I).

The compounds of formula (I) all have an asymmetrically substituted carbon atom in the α-position of the radical Ar. Each of these compounds therefore exists in two stereoisomeric forms as optical antipodes, one denoted by D (-f) in the following having the D-configuration and clockwise rotation, measured under the specified conditions, and the other as Ii (-) denoted the L-configuration and has a left-handed rotatability. The D (+) - and L (-) - noises of the compounds of the formula (I) are the subject of the invention, as well as the optically active or racemic mixtures of these D (+) - and L (-) - forms. In the following, the racemic compounds are represented by the designation (D, Ji) ,

Various pyrrolidin - ^ - one derivatives have already been used in the Described in literature and some of them as herbicides.

In the German patent specification 1 262 277 compounds are described, which can be used as intermediates for the manufacture of pharmaceutical products, dyes and insecticides are and which of the general formula

• η ι 3

¹ y

O * 2

where R ¹ ^, R « ₂ , R ¹ , and R '. each represent a hydrogen atom or an alkyl, cycloalkyl, aralkyl or aryl radical with a maximum of 8 carbon atoms.

This very general formula includes a large number of compounds, however, the examples of this patent relate to compounds

90S884 / 0557

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where R ^1. , a hydrogen atom or a methyl, phenyl or p-iolyl radical; they are therefore outside the general formula given here.

Furthermore, in DE-OS 19 25 198 her / tr "cide compounds the porinel

"V

R ".

in which R "., an optionally substituted alkyl, alkenyl, aralkyl, alkylene cycloalkyl, cycloalkyl or alkoxyalkyl radical, R" _{2 is} a crotyl, butyl, isopentenyl or isopentyl radical and R " _{5 has} the same meaning as R "has ₂ or denotes a hydrogen atom or forms an oyelohexyl radical _{with R" 2.}

This DE-OS relates essentially to ΪΓ-Cycloalky! Pyrrolidin-2-ones, which are different from the compounds of the invention. The only U-aralkyl derivatives mentioned in this DS-OS are H-benzyl-3-crotyl-pyrrolidin-2-one and N-benzyl-3-butyl-pyrrolidin-2-one, which are outside the general formula given above and none for those in the DE-OS mentioned There is an indication of the herbicidal properties.

It has now been found that in the case of i-benzyl-pyrrolidin-2-one derivatives the presence of a (Cj-C ^ -alkyl substituent on the Carbon atom in the α-position on the benzyl radical brings about a significant improvement in the herbicidal activity and that the (D, L) -1 - (a-alkyl-benzy3) -pyrrolidin-2-one derivatives according to the invention accordingly very generally have a significantly higher herbicidal activity than that of homologous 1-benzyl-pyrrolidin-2-ones.

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The compounds of the invention are made by a method which includes the following stages:

Step 1; Implementation of an ö ^ Chloralkanoylehlorids with an Aain the formula (III) according to the following reaction scheme:

Ar - CH - NH ₉ + Cl-CO-CH - CH - CHCl p? Ar-CH-NH-CO-CH-CH-CK-CI

t ^Z ill I III

R _{1 (III)} R ₃ R ₄ R ₅ R ₁ R ₃ R ₄ R ₅

+ HCl

wherein one of the substituents R ,, R- or R _{5 is} a methyl radical or a hydrogen atom and the other are sin ¥ hydrogen atom. - -.

Exe reaction of a hydrogen chloride carried out at a lemperatur between 0 and 50 ⁰ C in an aqueous-organic medium such as a mixture of water and Iiethylenehloriü in the presence consisting of an inorganic base, preferably one "operating at a Eemperatur between 0 and 25 ⁰ C in the presence of of sodium hydroxide _a

Stage 2: Cyclization of the compound formed in the previous stage according to the following reaction scheme

Ar-CH-KH-CO-CH-CH-CH-Cl ■> Ar-CH -N tj _{R. H} «,

C tot- υ "» ** HUA

I »RRR 1?

'i 3 4 5 ^K i

where ir, B. ^ _& Pw ₉ IL and R ^ have the meaning given above and S _{9 has} the same meaning as in! formula (I) *

The reaction takes place at a temperature between about 30 and about 100 ⁰ C in an aqueous-organic medium such as a mixture of water and methylene chloride in the presence of a phase

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transfer catalyst and a hydrogen chloride acceptor from an inorganic base in concentrated aqueous solution, for example sodium hydroxide.

As a phase change catalyst you can äie. Use catalysts of the quaternary ammonium type, as they are, for example, in Rosz. Chem. 39, p. 1223, 1965. In practice, good results are obtained, you Weian as a catalyst Benz3 "ltriäthylammoniumchlorid used.

For each of the compounds of the formula (I), the B (+) - or Ii (-) isomers according to the general procedure described above are produced, indom of a D (+) - or Ii (-) - amine of the formula (III) it is assumed that, in turn, the corresponding (D, l) -amines are separated by means of L (-) - malic acid and D (+) - tartaric acid after the one in Org. Synth. Coll., Vol. 2, page 459 (French edition) is obtained. .

The (D, l) -amines of the formula (III) are known in the plural; known processes A, B or C can be produced:

Procedure A

Action of ammonium formate on a ketone and subsequent Hydrolysis of the product obtained in an acidic medium according to the following reaction scheme

Ar-C = O + H-COONH- 2> Ar-CH-NH-CKO -> Ar-CH-NH ^

I * u ⁺ t 2

wherein Ar and R- have the same meaning as in formula (I),

This reaction, which is known as the Leuekardt reaction, is in Org. React, Vol. 5, ^ page 301 (1962).

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Procedure B

Reduction of an oxime according to the following reaction scheme

Ar-C = N-OH J " Ar-CH-NH ₉ + H, 0

wherein Ar and R. have the same meaning as described above.

The reducing agent used is either üiatriun in alcoholic Milieu (Acta Pharm. Sueeica5j page 429, 1968) or hydrogen in the presence of Raney-Iiekel (Bull. Soc. Chim. I'rance (5)? 4, page 1121, 1937).

Procedure G

Amination and reduction of a ketone according to the following scheme

Ar-C = O + NH + H>? - Ar - CH - NH

+ H>? - Ar - CH - NH ₀

wherein Ar and R. have the meaning given above, where in Presence of Raney-Wiekel after the one in Compt. Rend. Aca. May be. 207, page 545, 1938 described method is worked.

The following examples are intended to illustrate its manufacture and properties explain the compounds according to the invention in more detail without limiting them.

Example 1 Preparation of (l), Ii) -1- (2'-Hethoxy-q - methyl-benzyl) - DYrroliain-

2-on (compound Mr. 1)

In a three-necked flask with a volume of 2 liters, which is stirred mechanically and with a 250 ml dropping funnel, a thermometer

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and a rising cooler is provided »one gives 151 g (1 mol) of orthomethoxy-a-methylbenzyl-amine, 400 ml of methylene chloride, 1.1 mol of sodium hydroxide lozenges in 500 ml of water and the mixture is in an ice bath at about 5 ⁰ C cooled with vigorous stirring.

14-5.5 g (1 mol) of 97% 4-chlorobutyroyl chloride are then added dropwise, dissolved in 100 ml of methylene chloride, pour in

at such a rate that the temperature in the flask remains between 5 and 10 ° C.

Mach completion of 2ufließens keeping the Reaktionsteilnehner ncch for 15 minutes with vigorous RühreJ ₁ The reaction mixture is then transferred to a disc funnel (2 1), of which only the methylene chloride fraction is recovered.

The i-ethylenechloride solution obtained in this way is transferred to a three-necked flask with a volume of 2 liters, which contains 11.4 g (0.05 mol) of benzyltriethylammonium chloride, into which 400 g of aqueous 50% sodium hydroxide solution (5 mol ) admits. The mixture is stirred vigorously and dan \ i for 2 hours, heated to reflux (44 ⁰ C). A control by vapor phase chromatography indicates that the reaction has ended. After cooling in the water bath, 400 ml of water are poured into the flask, which causes the sodium chloride to dissolve and the system to settle.

Compartment and decant the reaction mixture into a separatory funnel the methylene chloride phase is obtained from 2 1 content. The aqueous phase is extracted with 200 ml of methylene chloride and the extract obtained is combined with the main organic phase, which is then washed with 200 ml of η-hydrochloric acid and then with 3 x 200 ml of water.

After drying and evaporation of the solvent to ¹

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206 g of a crude product are obtained which are purified by distillation.

Are thus obtained 196 g of (D, L) -1- (2-methoxy ^{t-a-methyl-benzyl)} -pyrrolidin-2-one having the following properties: Boiling point (0.25 mm Hg): 125 ⁰ C.

η * ⁰ = 1.543 Elemental analysis:

Calculated! 71 , 23 7th , 76 Found : 71 , 61 7th , 96

6.39 6.15

The yield is 89.5

¥ hen one by the method described in Example 1 operates, starting clay appropriate starting materials, the compounds are 2-to 15 produced whose physicochemical properties in the following 'labe-Pe are summarized. (In this table, Sp means the boiling point and Έ the melting point.)

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Z.SSO / 788606

Ar-

CH

R,

- N

Ur. the
Connect
manure Configu
ration - < Ar "1 ^R 2 Gross-
, formula physi
cal constants
th The end-
■ prey
Jt 'Elemental analysis
Calcpet Found. 76.19
7.94
7.41 74.42
7.97
7.18 2 (D, L) < X) / ^CH 3 , H
\ C ₁₂ H ₁₅ NO n ^ ^O : l, 545 56.7 C%
H%
N% 64.43
6.26
6.26 64.31
6.24
6.12 3 (D, L) c:
< CH ₃ H C ₁₂ H ₁₄ OO Sp: 125-126 ⁰ C
/ 0.05 mm Hg 60.1 C%
H%
N% 64.66
6.26
6.26 ' 63.63
6.35 4th (D, L) F ^ CH ₃ H n ^ °: 1.556 63.9 C%
H%
N% 69.56
6.76
6.76 69.21
6.98
6.92 5 (D, L) CH ₃ H TO T A n ^ ⁰ : l _f 52 € 72.5 C%
H%
N% 76.85
8.37
6.90 76.36
8.39
6.52 : 6 (D-, L, CH ₃ H C _n H ₁₇ NO n ² °: 1.540 62.1 C%
H%
N% 72.87
8.50 '
5.67 ' 72.64
8.51
5.71 7th (D, L) CP ₃
< 0-CH (CH ₃ ) ₂ • "irr
..I ₃ H ^C 15 ^H 21 ^NO 2 n ^ °: 1.530
Sp: 122 ° C /
0.05 nunHg 76.2 C%
H%
N% 60.70
5.45
5.45 60.93
5.58
5.46 8th (D, L) CH ₃ H C ₁₃ H ₁₄ P ₃₁₁ O n ^ ° il, 49O
Sp: 108 ⁰ C /
0.01 rnmHg 77 C%
H%
N%

4SS0 / V98806

Ar-CH- N. ■ R,

No. of link

configuration

R,

Gross formula

physical KöJi- *
stanten

yield

Elemental analysis Calculated Found

(D, L)

Cl

CH-

r £ °: 1.568

Sp: 132 ⁰ C /
0.03 mmHg

64

C% 55.81 55.72 H% 5.04 5.30 N% 5.43 5.19

(D / L)

-C ₂ H

₂ H ₅ .

64

C%

H%
N%

76.85
8.37
6.90

76.64 8.31 6.78

(D, L)

© ■

-CH- (CH ₃ )

: 1.530

66

C%

11%
N%

77.42
8.76
6.45

76.68

8.75 6.32

(D, L)

-CH.

C ₁₃ H ₁₇ NO

n £ °: 1,532

Sp: 11O ⁰ C /
0.015 nrollg

65.5

C%

H%
N%

7 ^, 0.5
8.37
6.90

76.66 8.49 6.81

(D, L)

-CH,

n ^ °: 1.646

Sp: 128 ⁰ C /
0.03 rnrilg

72

H%
N%

65.68
6.74
5.89

65.74 6.93

ς ι λ

(D, L)

OCH.

-CH,

S _p : 13O432 ^e C /
0.05 mmHg

49

C%

H%
N%

72.10

8.15
6.01

71.24 8.23 5.98

(D, L)

-CH.

C ₁₃ H ₁₇ NO

n ^ °: 1.537

Sp: 12O ⁰ C /
0.12 mmHg

49

C%

H%
N%

76.85
8.37
6, .9O

75.82 8.45 6.31

ISS0 / V88606

Ar

/ π

- CH - N -—L

R,

ITr. de:
Connect
manure

configuration

Ar

Gross-

formula

physical constants'

yield

Elemental analysis
Calculated Found

(D, L)

C ₁₇ H ₁₇ NO

F ™ 135.4 ° C

70

C% 81.27
H% 6.77

N% 5.58

81.25
7.2
5.5S

Example 3 Production of

din-2-one (compound 1A), optical D (+) - isora of the compound Fri »1

This compound is generally prepared by the method described in Example 1, starting from 4-chlorobutyroyl chloride and D (+) ~ o-methoxy-a-methylbenzylamine with the rotating power
JYes] ρ = + 37 ° (without solvent) * which in turn is produced by the separation of (D, Ii) -o-methoxy-a-methyl-benzyl-amine according to the method described in Org »Synth" Coll., Vol. 2, page 459 ( French edition) described method was obtained *

The physicochemical properties of Compound 1A thus obtained are as follows:
[«3 τι = ⁺ 90 ° (0 = 0.1 in anhydrous ethanol)

optical purity: 90

η ²⁰ = 1.5492

Efo 6.39 7.76 6.35 7.82

Boiling point: 12O ° C / O5 mm Hg « Elemental Analysisϊ

Calculated: "^ 23

Found: 70.25

Example 4

Preparation of D (4Q- 1- (a-Helyl-benzyl) -pyrrolidin-2-one (compound 2A _f D (-f-) - isomer of the compound - Mr. 2
The procedure is as in the previous example, except that the benzylamine used in this example has been replaced by commercially available D (+) - a-methylbenzylamine with the rotation ability [ _a J = + 39 ° (without solvent)
Compound 2A has the following properties1
[a] _D a + 19 »5 ° (0 = 0.1 in anhydrous ethanol)

Boiling point 108 ° C / 0.06 mm Hg

Elemeataranalysei - ^

Bereciinet: 76.19 "7 _S 94

Found: 75.46 8.09

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example 5 Herbicidal activity in advance "in crops and harmful plants

or weeds

In pots of 9 χ 9 χ 9 cm, which are filled with light soil a certain number of grains are sown depending on the type of plant and the size of the grain.

The grains are then covered with a layer of earth for about 3 minutes Thickness.

After moistening the earth, the pots are sprayed with an amount of broth per pot corresponding to a volume of 500 l / ha, which contains the active material in the dose considered.

The broth is prepared by diluting an emulsifiable concentrate with the following composition by weight: active substance to be tested 20 fo

Emulsifier:! Tony! Phenol, with 17 moles of ethylene

oxide oxethylated $ 10

solvent (xylene) 70 #

One then brings to the desired dilution, which contains the active limaterial in the desired dose. The trials are for dose levels of active material from 1 kg / ha to 8 kg / ha

causes.

The treated pots are then placed in troughs, which are intended to receive the irrigation water by irrigation from below, and are kept for 35 days at ambient temperature below 70 % relative humidity.

The occurrence of the neglect value is established after 35 days based on a control plant grown under the same conditions with an atomized dispersion without active material

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"had been treated firmly.

The plant species tested, both the crops and the weeds, were as follows: Weeds:

¥ oats (Avena fatu-a) I ¹ A

tall grass (Digitaria sanguinalis) DI

Millet (Eehinoehloa erus-galli) PA

Ryegrass, meadow newt (Lolium multiflorum) RA

Giant Foxtail (Setaria faberii) SE

Foxtail (Alopecurus myosuro'ides) VU

Crops

"Beanut (Arachis hypogea) AR

Oilseed rape (Brassica napus) CZ

Cotton (Gossypium barbadense) CiE

Bean (Phaseolus vulgaris) HA

Soy (Glycine max) SO

Litmus (Helianthus annuus) EO

Black beet (Beta vulgaris) "BB

Corn (Zea mays) MA

Korn (iriticum sativum) p

The "observed results" in the following table

are expressed as a percentage of destruction

of treated plants in relation to an untreated control sample.

The number 100 indicates that there was complete annihilation of the plant under consideration.

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cn cn - «a

Connect dose FA ■ Weeds ¹ PA ¹ κΑ - '■ VU AR ' CZ Crops HA ' SO ' TO BE '· MA ¹ BL manure
J) Jr. kg / ha 60
80
100 DI 90
100
100 90
95
100 ¹ SE 90
100
100 0
0
30th 0
0
20th • _CT ι 0
0
80 0
• ο
10 0
0
30th 0
0
0 0
0
80 0
30th
90 X 1
2
4th 80
100 70
100
100 100
100 90
100 40
100
.100 100
100 15th
60 0
30th 0
0
50 . . - 0
30th 0
0 0
15th 30th
90 0
80
I. IA 1 ^;
4th 80
70 90
100 60 '
90 85
100 50
100 30th
85 0
0 0
15th 0
40 0
S.
0 0
0 0
0 0
0 0
0 0?
10
• 2
ν 4th
8th 70 20th
85 100 9f5 0
25th 100 0 0 0
0 0 0 0 0 '' 0 Ό 2A 4th 0
30th 85 100
100 80
100 0 60
100 0
0 0
0 0 0
0 0
0 0
0 0
0 0
0 0
15th 3 2
4th 30th 30th
100 ICO 100 30th
90 80 0 25th • Ό
0 0 10 0 0 0 30th 4th 8th 80 95 80 90 80 100 20th 15th ο · 0 0 0 15th 0 40ΡΟ ' 5 8th 50 100 100 100 40 100 0 0 0 0 0 0 10 0 9 8th 95 95 10

Example 6 comparison attempt

In this experiment, the herbicidal activity on weeds in the First run in doses of 1 and 2 kg / ha of the following compounds

compared:

1- (2 ^f -Methoxy-benzyl) -pyrrolidin-2-one (comparison compound), (D, L) -1- (2 ^l -Metlioxy-a-metnyl- "benzyl) -pyrroliain-2-one (compound

1).

The method used is as described in Example 5 is. The results observed are summarized in the table below, with the designation used is the same as in Example 5.

Dosts
kg / ha FA DI PA RA • • SE VU Ver
equal
connect - 1
2 O
O 60
85 20th
80 O
5O O
30th O
60
j "Comparison
X *. «L 1
2 60
80 70
100 90
100 90
95 40
100 90
100

This comparison shows that in the case of the i-benzyl-pyrrolidin-2-one derivatives the presence of a methyl substituent on the carbon in the α-position in the benzyl radical is a very significant improvement the herbicidal effectiveness brings with it.

The results described in Examples 5 and 6 show the good herbicidal activity of the compounds according to the invention.

In general, the compounds according to the invention have, in particular, when ahead of crops and weeds

909884/0557

have good herbicidal activity against grass weeds on and a good selectivity towards cultivated plants like corn, beetroot, peanuts, rapeseed, cotton, beans, soy, litmus. In the case of (D, L) -1- (2-methoxy-a-methyl-benzyl) -pyrrolidin-2-one (Compound 1) excellent results were obtained, which in the forerunner in a dose of 2 kg / ha completely finger grass, Millet, giant foxtail and foxtail destroyed and a satisfactory herbicidal effectiveness against wild oats and Y / Hiesenlolch, this dose of the majority of the crops in question is well tolerated.

Excellent results were also obtained in the case of Compound 1A obtained, which leads to the largest rope from the D (+) - iso'aeren of 1- (2-methoxy-a-methyl-benzyl) -pyrrolidin-2-one and to a low one The rope consists of the! (-) - isomers of the same compound.

For the herbicidal treatments by means of the compounds according to the invention, the dose of active material to be used can be vary from 0.5 to 10 kg / ha, depending on the compound used, the type of crop and the nature of the soil. Preferably this dose is between 1 and 6 kg / ha.

For use in practice, the compounds of the invention are rarely used alone. Most of the time they are part of compositions which, in addition to the active material according to the invention, generally includes a carrier and / or a surface-active Include agents which are agriculturally useful and compatible with the active material.

The term "carrier" denotes in the context of the present statements an organic or mineral, natural or synthetic material with which the active material is associated is to facilitate its application on the plant, on the grain or the soil and its transport or its handling. The support can be solid (tones, natural or

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synthetic silicates, resins, waxes, solid fertilizers) or fluid (water, alcohols, ketones, petroleum fractions, chlorinated Hydrocarbons, liquefied gases).

The surface active agent can be an emulsifying, dispersing or Wetting agents and be ionic or non-ionic. One can for example the salts of polyacrylic acids, of magnesium sulfonic acids, condensation products before ethylene oxide with petroleum alcohols, fatty acids or call fat women.

The compositions of the invention can be in the form of wettable Powders, powders for atomization or for sprinkling, granules, solutions, emulsifiable concentrates, emulsions, concentrates are produced in suspension and aerosols.

The wettable powders are usually prepared so that they contain 20 to 95 wt. -I <> of the active ingredient and usually also contain a solid carrier-Lger, from 0 to 5 weight ^ wetting agents, 3-10 wt ^ one or more stabilizers and / or other additives such as penetrants, adhesives or anti-clotting agents, dyes, etc.

As an example, the following composition is a wettable

Powder listed:

active material (compound no. 1) 50 $>

Calcium Lignosulfate (Deflocculant) $ 5

anionic wetting agent 1 %

non-clumping silicon dioxide 5 %

Kaolin (Ilillstoff) 39%

The granules which are intended to be applied to the ground are usually produced in such a way that they have dimensions between 0.1 and 2 mm and they can be produced by agglomeration or impregnation. In general

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The granules will mean 0.5 "to 25% by weight of active material and 0 to 10 wt .- ^ additives such as stabilizers, Contains slow release modifiers, binders and solvents.

The emulsifiable concentrates, which can be used by atomization are generally contained in addition to the solvent and, if necessary, a cosolvent 10 to 50 pounds w / v. at active material, 2 to 20 # w / yoI. suitable additives such as Stabilizers, penetrants, corrosion inhibitors and dyes, as well as adhesives.

The following is an emulsifiable concentrate as an example where the quantities are expressed in -g / l:

active material (compound Mr. 1) 400 g / l

Alkali dodecylbene sulfonate. 24 g / l

Nonylphenol, oxethylated with 10 mol of ethylene oxide 16 g / l

Cyclohexanone 200 g / l

Add aromatic solvent to 1 1

The concentrates in suspension, which also z: <: u atomize are applicable, are prepared in such a way that a fluid stable product is obtained that does not settle and they usually contain 10 to 75 wt. active material, 0.5 to 15 wt. surfactant, 0.1 to 10 wt. thixotropic Medium, 0 to 10 wt .- ^ suitable additives such as antifoam agents, Corrosion inhibitors, stabilizers, penetrants and adhesives and as a carrier water or an organic ! Liquid in which the active material is essentially insoluble is: Certain solid organic materials or mineral salts can be dissolved in the carrier to prevent sedimentation Avoid or use as antigels for the water.

Aqueous dispersions and emulsions, for example compositions

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tongues made by diluting a "wettable powder or a obtained emulsifiable concentrate according to the invention by means of water also fall within the scope of the invention. The emulsions can be of the water-in-water or the oil-in-water type be and si3 can have a chewy consistency like that of a "mayonnaise".

The compositions of the invention can also contain other ingredients for example protective colloids, adhesives or Yerdikkrragsmittel, theseotropic agents, stabilizers or sequestering agents as well as other known active materials with pesticide properties, particularly insecticides or! fungicidal.

909884/0557

Claims (12)

Claims in which the individual symbols have the following meanings ": Ar denotes a phenyl radical _s which is optionally substituted by 1 to 2 identical or different substituents, which are selected from halogen atoms, alkyl radicals with 1 to 4 carbon atoms and alkoxy radicals with 1 to 4 Carbon atoms, alkenyloxy radicals with 2 to 4 carbon atoms, alkynyloxy radicals with 2 to 4 carbon atoms, hydroxyl, nitro, Sri fluorine thy Ij, monoalkylcarbamoyl with 1 to 4 carbon atoms in the alkyl part, dialkylcarbamoyl ₅ where each of the identical or different alkyl parts has 1 to 4 carbon atoms, aliphatic Acylamino with 2 to 5 carbon atoms, or a radical Ar "-Ο-, where Ar" is an optionally substituted phenyl radical or a heterocyclic radical with 6 chain members j, optionally substituted and containing as heteroatoms an oxygen »sulfur or nitrogen atom, or Ar denotes an optionally substituted aromatic heterocyclic radical with 5 to 6 chain members and containing as heteroatom 1 to 2 identical or different atoms selected from nitrogen, oxygen or sulfur, R ₁ denotes an alkyl radical with 1 to 4 carbon atoms, a cyeloalkyl radical with 5 to 6 carbon atoms or one 909884/0557 optionally substituted phenyl radical, Rp denotes a hydrogen atom or the methyl radical, 2. A compound according to claim 1 of the formula ^R 2 wherein X is an atom or a radical selected from the halogen atoms, the alkyl radicals with 1 to 4 carbon atoms, the alkoxy radical with 1 to 4 carbon atoms and tem erifluoromethyl radical, ^ ₈ -J. η is an integer equal to 1 or ^ where, if η is 2, the substituents Y can be identical or different, R ,. un3 denotes an alkyl radical with 1 to 3 carbon atoms or the phenyl radical
R2 has the same meaning as given in claim 1. 3. Compound according to one of claims 1 or 2, characterized in that that they consist of an optically active or racemic mixture of the optical isomer of configuration D (+) and the optical isomer of configuration L (-). 4. A compound according to claim 3, characterized in that the compound is (D, L) -1- (2 ~ methoxy-a ~ methyl-benzyl) -pyrroli- din-2-one . 5. A process for preparing a compound according to claim 1, characterized in that in a first stage an amine of Pormel Ar-CH- HH ₂ wherein Ar and R ₁ the check-in claim 1 Have given meaning, with a / ^ - Chloralkanoylehlorid 909884/0557 the Eormel Cl - CO - CH - CH - CH - Cl I I £ S. ·? Κ. «Κι- 5 4 5 converts, in which one of the substituents IU, R. and Rf- is a hydrogen atom or a liethyl radical and the others a hydrogen atom, so there? a compound of the formula Ar -OH - HH - CO -CH - CH - CH - Ci I ifi ■ β "DOT? ¹ H ^ 4 5 is formed, in which Ar, R,., R ,, R. and R ₅ have the meaning given above and that in a second stage, the compound resulting from the previous stage is cyclized. 6. The method according to claim 5, characterized in that the first stage is carried out in an aqueous-organic medium in the presence of an inorganic ^
performs. inorganic base at a temperature between ü and 50 ⁰ C 7. The method according to claim 5, characterized in that the second stage is carried out in an aqueous-organic medium at an oil temperature between 30 and 100 ⁰ C in the presence of an inorganic base and egg: ies phase transition catalyst. .by ^ 8. The method according to claim 7XgÖEennzelehnet that the phase change catalyst which is benzyltriethylammonium chloride. 9 · Herbicidal composition for use in agriculture characterized in that it is an effective material as an active material An amount of at least one compound according to any one of claims 1 to 4 contains. 9098 * 4/0557 10. The composition according to claim 9, characterized in that it, in addition to the active material, a carrier and / or a Surface-active agent, which can be used in agriculture and are compatible with the active material. 11. Composition according to claim 9, characterized in that it contains 0.5 Ms 95 wt .- ^ active material. 12.Methods for selective weed control of maize, beet, peanut, rapeseed, cotton, bean, soy or lacquer mucus, characterized in that a composition according to one of the claims is applied to these cultures or in their immediate base 9 to .11 applies or applies. 909884/0557