DD142143A5 - HERBICIDAL COMPOSITION - Google Patents

Description

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The invention relates to a process for the preparation of novel pyrrolidine-2-one derivatives and to the herbicidal compositions containing them.

Characteristic of the known technical solutions

Various pyrrolidin-2-one derivatives have been described in the literature and some of them as herbicides »

In DE-PS 1 262 277 compounds are described which are useful as intermediates for the preparation of pharmaceutical products, dyes and insecticides and which are of the general formula

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in which R ' _{1 #} R' ₂ , R ¹ ^ and R ^{1 '} each represent a hydrogen atom or an alkyl, cycloalkyl, aralkyl or aryl radical having at most 8 carbon atoms

This very general formula comprises a large number of compounds ·:

Furthermore, in DE-OS 1,925,198 herbicidal compounds of the formula

R "- - IT ¹ ^

R " ₃

wherein R "is an optionally substituted alkyl, alkenyl, aralkyl, Alkylencycloalkyl-, cycloalkyl, or alkoxyalkyl radical, R" _{2 is} a crotyl, butyl, isopentenyl or Isopentylrest and R ¹ U the same meaning as R " ₂ has or denotes a hydrogen atom, or forms a cyclohexyl radical with R" ₂ .

This DE-OS relates essentially to IJ-cycloalkylpyrrolidin-2-ones, which are different from the compounds according to the invention. The only U-aralkyl derivatives _{9 mentioned} in this DE-OS are the H-benzyl-3-crotyl-pyrrolidine 2-one and the H-benzyl-3-butyl-pyrrolidin-2-one, v / elche are outside the general formula given above and for which there is no indication of the herbicidal properties in the abovementioned DE-OS.

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The known PR-PS 2 048 507 relates to the compounds of DE-OS 1 925 198.

Object of the invention

The object of the invention is to provide a simple and economical process for the preparation of novel pyrrolidine-2-one derivatives having strong herbicidal properties which are suitable for the selective weed control in crop plants.

Explanation of the essence of the invention

The invention has for its object to find new compounds with very good herbicidal properties and suitable A-agangskomponenten and suitable reaction conditions for their preparation «

It has now been found that in the case of 1-benzylpyrrolidin-2-one derivatives, the presence of a (CL-CO-alkyl) substituents on the carbon atom in the position on the benzyl radical is a significant improvement in herbicidal activity void, therefore, that the (D, L) -1- ( cC- alkylbenzyl) -pyrrolidin-2-one derivatives according to the invention generally have a markedly higher herbicidal activity than that of homologous 1-benzylpyrrolidin-2-ones "

According to the invention, compounds of the general formula

Ar CH IT

R ₁ ¹ 0

manufactured"

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wherein the individual symbols have the following meanings: Ar is a phenyl radical which may optionally be substituted by 1 to 2 substituents which are identical or different from one another, selected from the halogen atoms, the alkyl radicals having 1 to 4 carbon atoms, the alkoxy radicals of 1 to 4 carbon atoms, the alkenyl oxyresines of 2 to 4 carbon atoms, the alkynyloxy groups of 2 to 4 carbon atoms, hydroxyl, methane, irifluoromethyl, monoalkylcarbamoyl of 1 to 4 carbon atoms in the alkyl moiety, dialkylcarbamoyl wherein each the alkyl moieties which are identical or different from each other, comprises 1 to 4 carbon atoms, aliphatic acylamino having 2 to 5 carbon atoms or an Ar'-O radical, wherein Ar 'represents an optionally substituted phenyl radical or a heterocyclic radical having 6 chain members, the given if substituted and containing as heteroatom an oxygen, sulfur or nitrogen, bede ood; Ar can also be an optionally substituted aromatic heterocyclic radical having 5 to 6 chain members, which contains as hetero atoms 1 to 2 identical or different atoms selected from the nitrogen, oxygen or sulfur atoms. , R .. represents an alkyl radical having 1 to 4 carbon atoms ^ a cycloalkyl radical having 3 to 6 carbon atoms or an optionally substituted phenyl radical; Rg represents a hydrogen atom or the methyl radical

According to the invention, the 1-benzylpyrrolidin-2-one derivatives of the formula

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manufactured, . ^r ...

wherein the individual symbols have the following meanings: Y is an atom or a radical selected from halogen, alkyl radicals having 1 to 4 carbon atoms, alkoxy radicals having 1 to 4 carbon atoms and the trifluoromethyl radical, η is an integer equal to 1 or 2 with the Given that, if η = 2, the substituents Y may be identical or different,

R ₁ is an alkyl radical having 1 to 3 carbon atoms or a phenyl radical, R p has the meaning given for formula (I) ·

The compounds of formula (I) all have an asymmetrically substituted carbon atom "in <£ position of Ar Each of these compounds exists therefore in two stereoisomeric forms as optical antipodes, the one with D (+), referred to hereinafter, the D Configuration and dextrorotatory rotation measured under the given conditions, and the other as L (-) designated L configuration and levorotatory rotation property. The D (+) and L (-) forms of the compounds of the formula (I ) are the subject of the invention and the optically active or racemic mixtures of these D (+) and L (-) forms. In the following, the racemic compounds are represented by the designation (D, L).

The compounds of the invention are obtained by a process comprising the following steps:

Step 1: Reaction of a Γ-chloroalkanoyl chloride with an amine of the formula (III) according to the following reaction scheme:

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Ar-CH-M,

(III)

Cl-CO-CH - CH - CHCl I I

Ar-CH-HH-CO-CH-CH-CH-Cl

III. ^R 1 ^R 3 ^R 4 ^R 5

+ HCl

in which one of the substituents Ro »Ra or R, - denotes a methyl radical or a hydrogen atom and the others a hydrogen atom ·

The reaction is carried out at a temperature between 0 and 50 ⁰ C in an aqueous-organic medium such as a mixture of water and methylene chloride in the presence of a hydrogen chloride acceptor consisting of an inorganic base, preferably working at a temperature between 0 and 25 ⁰ C in the presence of sodium hydroxide ·

Step 2: Cyclization of the compound formed in the previous step according to the following reaction scheme:

Ar-CH-ITH-CO-CH-CH-CH-Cl

ιιιι

R ₁ R ₃ R ₄ R ₅

R ₂ + HCl

in which Ar, R-, R 1, R 1 and R ₃ have the abovementioned meaning and R _{2 has} the same meaning as in formula (I)

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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 s chloride in the presence of a phase transfer catalyst and a Chlorwasserst offakzeptors consisting of an inorganic base in concentrated aqueous solution, for example sodium hydroxide ·

As a phase transition catalyst can be used the catalysts of the quaternary ammonium type, as used for example in Rosz. Chem. 39, page 1223, 1965. In practice, good results are obtained when using as catalyst benzyltriethylammonium chloride ·

For each of the compounds of formula (I), the D (+) or L (-) isomers may be prepared according to the general method described above by substituting a D (+) <- or L (-) ) Amine of the formula (III), which in turn is prepared by separating the corresponding (D, L) amine by means of K-) -malic acid and D (+) -vitic acid according to the method described in Org. Synth. Coll., Vol , Page 459 (French edition).

The (D, L) -amines of the formula (III) are known in the majority, they can be prepared by one or the other of the processes A, B or C known per se, which follow.

Method A. , ,

Exposure of ammonium formate to a ketone and subsequent hydrolysis of the resulting product in an acidic medium according to the following reaction scheme

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'H ₂ O'

Ar-C = O + H-COOKH-> Ar-CH-NH-CHO ---> Ar-CH-NH ₅

U ⁴ IH ⁺ I ²

R ₁ ^R 1 ^R 1

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

This reaction, known as the Leuckardt reaction, is described in Org. React., Vol. 5, p. 301 (1962).

Method B

Reduction of an oxime according to the following reaction scheme

Ar - C = N - OH ^ Ar - CH - NH ₂ + E ₀ O

R ₁ R ₁

where Ar and R _{1 have} the same meaning as above

The reducing agent used is either sodium in an alcoholic medium (Acta Pharm. Suecica 5, page 429, 1968) or hydrogen in the presence of Raney nickel (Bull. Soc. Chim. Prance (5), 4, page 1121, 1937).

Method C ......

Amination and reduction of a ketone according to the following scheme

Ar-C = O + NH-, + E ₀ »Ar - CH- NH ₀

ι 3 2 'ι 2

R ₁ R ₁

wherein Ar and R ₁ are as defined above,

in the presence of Raney nickel according to the in Compt. Rend. Aca "Be. 207, page 345, 1938.

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embodiment Example 1 .

Preparation of (D, L) -1- ( ^2f ~methoxy) <£ -methylbenzyl) -pyrrolidin-2-one (compound m.fr. 1)

In a 3-necked flask of 2 liters, which is mechanically stirred and fitted with a 250 ml dropping funnel, a thermometer and an ascending condenser, 151 g (1 mol) of ortho-methoxy-oC-methyl-benzyl-amine are added, 400 ml of methylene chloride, 1.1 mol of sodium hydroxide pastilles in 500 ml of 7 / asser and the mixture is cooled in an ice bath at about 5 ⁰ C with vigorous stirring ·

145.5 g (1 mol) of 97% strength 4-chlorobutyroyl chloride, dissolved in 100 ml of methylene chloride, are then added dropwise at such a rate that the temperature in the flask remains between 5 and 10 ^° C.

After completion of the feed, the reactants are kept under vigorous stirring for a further 15 minutes. The reaction mixture is then transferred to a disk funnel (21), of which only the methylene chloride fraction is recovered.

The methylene chloride solution thus obtained is transferred to a 3-necked flask of 2 liters contents containing 11.4 g (0.05 mol) of benzyltriethylammonium chloride, in which 400 g of aqueous 50% sodium hydroxide solution (5 mol) is added rapidly. The mixture is stirred vigorously and then heated to reflux for 2 hours (44 ⁰ C). Sine control by vapor phase chromatography indicates that the reaction is complete.

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When cooling in a water bath, pour into the flask 400 ml of water, which makes the dissolution of the sodium chloride and the discontinuation of the system nervous ·

After decanting off the reaction mixture into a separatory funnel of 2 1 content, the methylene chloride phase is obtained. The aqueous phase is extracted with 200 ml of methylene chloride and the resulting extract is combined with the main organic phase, which is then washed with 200 ml of η-hydrochloric acid and then with 3 × 200 ml of water is washed *

After drying and evaporation of the solvent to dryness, 206 g of a crude product are obtained which are purified by distillation. "

This gives 196 g (D, L) -1- (2'-MGtIiOXy- <£ methyl-benzyl) -pyrrolidin-2-one having the following properties: Boiling point (0.25 mm Hg): 125 ⁰ C.

n £ = 1.543

Elemental analysis: C % H % 'N % Calculated: 71.23 7, 76 6 39 Found: 71.61 7, 96 6 15

The yield is 89.5 % * Example 2

Working according to the procedure described in Example 1, starting from suitable starting materials, compounds 2 to 15 are prepared whose physicochemical properties are summarized in the table below. (In this table, Sp is the boiling point and P is the melting point.)

Ar-CH-H

2? R. the Konfi-Verbinguradung tion

I ₁ R ₂ gross physical-. Elemental analysis

Formulary See Buy Calculated Found

constant.

(D, L)

n ^ ⁰ : 1.545

56.7 CSS

76.19 7.94 7.41

74.42

7,97 7,18

(D, L) / f% ~ ^{cl CH} 3 ^H C ₁₉ H ₁₇₁ ClIfO Sp: 125-126 ° C 60.1 ^{Λά Ί4} / 0.05 mm Hg

G% 64.43 E% 6.26 % 6.26

64.31 6.24 6.12

(D, L) Cl

OK- H .20

n £ ^v : 1,556 63,9

C% 64.66 H% 6.26 6.26

63.63, 6.35, 6.39

(D, L)

CH ₃ H 20

^ x 1,526 72.5

C% 69.56 where 6.76 6.76

69.21 6.98 6.92

(D ₉ L)

20

62.1

76.85 8.37 6.90

76.36 8.39 6.52

(D, L) O-CH (CH ₃ ) ₂ CH ₃ H

n °: 1,530

Sp: 122 ^° C / 0.05 mm Hg

76.2

C% 72.87 HSS- 8.50 5.67

72.64

8.51

• 5.71

Ar-CH-U

The Konfi-Varbinguradung tion

Ar

R ₁ · Rp gross formula

physical constants

'Elementary analysis

Loot Calculated Found

(D, L) CF ₃

CH ₃ H

nj x ⁰ : 1.490

Sp 1108 ⁰ C / 0.01 ram Hg

C% 60.70 5.45 5.45

60.93 5.58 5.46

(D, L)

C ₁₂ H ₁₃ Cl ₂ H ₂ PO ₄ °: 1.568

Sp: 132 ^° C /, 0.03 mm Hg

S 55.81 ό 5.04 "> 5.43

55.72 5.30 5.19

(D, L)

-C ₂ H ₅ H

₁₃ H ₁₇ H

ajp ί 1,534

76.85 8.37 6.90

76.64 8.31 6.78

(D, L)

-CH- (CH ₃ ) ₂ HC ₁₄ H ₁₉ HO nj ^u : 1.530 C% 77.42 ~ - 8.76 6.45

76.68

8.75 6.32

VaJ VjJ

(D, L)

-CH ₃ 3 -CH ₃ C ₁ ^

ng ^w j 1.532

Sp: 110 ^° C / 0.015 mm Hg 65.5

76.85 8.37 6.90

76.66

8.49 6.81

(D, L)

3-CH ₃ C ₁₃ H ₁₆ CUTO ng ^w : 1.646

Sp: 128 ^° C / 0.03 mm Hg

c% 65.68 65.74 Η% 6.74 6.93 Η% 5.89 5.74

Confederation

Ar R ₁ R ₂ gross

formula

physical constants

Elemental Analysis Loot Calculated Found

(D, L)

OCH

3 -CH ₃ 3-CH ₃

η * " ⁰ : 1.536

Sp: 130-132 ° C / 0.05 mm Hg

CJS 72.10

- * 8.15 6.01

71.24 8.23 5.98

V> J

-CH ₃ 5-CH ₃

²⁰

1,537 49

Sp: 120 ^° C / 0.12 mm Hg

33%

76.85 8.37 6.90

75.82 8.45 6.31

= 135.4 C 70

% 81.27 '6.77 5.58

81.25 7.2

5.59

VJL

- * O I

VaJ

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Example 3 ,

Herstelltaig of D (-t -) - 1- (2'-methoxy- <£ methyl-benzyl) pyrrolidine "2 ~ one (Compound 1A) Optical D (+) - isomer of the compound Ur, 1 ·, ..;. .:.

This compound 1A is prepared according to the procedure described in Example 1, starting from 4-chloro-butyroyl chloride and D (+) - o-methoxy- cC- methyl-benzyl-amine having the rotation CoCjF-Q - + 37 ° (without solvent), which in turn can be prepared by resolution of (D, L) -o-methoxy-β-methyl-benzyl-amine according to the method described in Org "Synth, Coll., Vol. ₀ 2, page 459 (French edition). was obtained

The physicochemical properties of the compound 1A thus obtained are as follows:. l ~ oCj ^ - + 90 (C = 0.1 in anhydrous ethanol) optical purity: 90 %

ηψ = 1.5492

Boiling point: 120 ° C / 0.05 mm Hg, elemental analysis: % H% U % Calculated: 71.23 7.76 6.39 Found: 70.2 $ 7.82 6.35

Example 4

Preparation of D (4 -) - 1 - ((-) - methylbenzyl) -pyrrolidin-2-one (Compound 2A, D (4) - isomer of the compound Hr, 2

The procedure is as in the previous example, except that the benzylamine used in this example by commercial D (+) ~ c ' methylbenzyl-amine with the turning ability

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= + 39 ° (without solvent) · The compound 2A thus obtained has the following properties:

CoCjj) = + 19.5 (C = 0.1 in anhydrous ethanol) Boiling point: 108 ° C / 0.06 mm Hg Elemental analysis : C% H % Έ% Calculated: 76.19 7.94 7.41

Found: 75.46 8.09 7j38

Example 5

Herbicidal activity in the run-up to crops and weeds or weeds

In pots of 9x9 cm, which are filled with light field soil, one sows a certain number of grains depending on the plant species and the size of the grain.

The grains are then covered with a layer of earth about 3 mm thick,

After moistening the soil, pots are treated by spraying with a quantity of broth per pot corresponding to a volume of 500 l / ha containing the active material in the considered dose.

The broth is prepared by diluting an emulsifiable concentrate having the following composition by weight:

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active substance to be tested 20 % Emulsifier: nonylphenol, oxyethylated with 17 moles of ethylene oxide 10 % solvent (xylene) 70 %

One then brings to the desired dilution containing the active material in the desired dose. The experiments are carried out for doses of active material of 1 kg / ha to 8 kg / ha ·

The treated pots are then forced to hold irrigation water from below and kept at ambient temperature below 70 % relative humidity for 35 days.

After 35 days, the occurrence of the extermination value with respect to a control plant treated under the same conditions with a sputtering dispersion without active material is determined.

The plant species tested, both the crops and the weeds, were the following:

·;. · ' .) ·:

Weeds ........

Wild oats (Avena fatua) PA

Pingergrade (Digitaria sanguinalis) DI

Millet (Echinochloa crus-galli) PA

Raigras, meadow lark (Lolium multiflorum) RA

Giant Swallowtail (Setaria faberii) SE

Foxtail (Alopecurus myosuroides) VU

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crops

Peanut TArachis hypogea) AR

Oilseed rape (Brassica napus) CZ

Cotton (Gossypium barbadense) GT

Bean (Phaseolus vulgaris) HA

Soy (Glycine max) SO

lackmus (Helianthus annuus) TO

Beetroot (Beta vulgaris) 'BE

Corn (Zea mays) MA

Grain (Triticum sativum) BL

The observed results, which are summarized in the following table, are expressed as percent destruction of the treated plants relative to an untreated control sample »

The number 100 indicates that complete destruction of the plant under consideration took place »

Verbin-dose weeds crops

tion. kg / ha PA · DI »PA ·. RA «SE» VU AR * CZ * CT »HA« SO »TO * BE · MA« BL

1 1 60 70 90 90 40 30 90 0 0 0 0 0 0 0 0 0 IO 2 80 100 100 95 100 90 100 0 0 0 0 0 0 0 0 30 _ ^ '4 100 100 100 100 100 80 100 30 20 50 80 10 30 0 80 90 CJ 1A 1 80 90 100 90 50 40 100 15 0 0 - 0 0 0 30 0 4 100 100 100 100 100 100 60 30 40 mm 30 0 15 90 80 Ui 2 4 80 20 60 85 0 30 0 0 0 0 0 0 0 0 0 1 8th 70 85 90 100 25 85 0 15 0 0 0 0 0 0 10 co 2A 4 70 85 100 90 0 100 0 0 0 0 0 0 0 0 0 I 3 2 0 30 100 80 60 0 0 0 0 0 0 0 0 0 4 30 100 100 100 100 0 0 0 0 0 0 0 0 15 4 8th 30 95 100 100 80 0 25 0 0 10 0 0 0 30 VJL 8th 80 100 80 90 100 20 15 0 0 0 0 15 0 40

50 95 100 100 95 100 0 0 10 0 0 0 10 "0 20 vS. ^

VJl -VC

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Example 6 Comparison Experiment

In this experiment the herbicidal activity on weeds in the forerunner is compared in doses of 1 and 2 kg / ha of the following compounds:

1- (2 ^{f-methoxy-benzyl)} -pyrrolidin-2-one (reference compound), (D, L *) -1- ^(2-methoxy-I · ^ methyl-benzyl) -pyrrolidin-2-one (Compound Mr. 1).

It is as described in Example 5, worked. The results observed are summarized in the following table, the designation used being the same as in Example 5.

dose PA DI PA RA SE VU kg / ha 0 60 20 0 0 Ό comparison 1 0 85 80 • 50 30 60 connection 2 60 70 90 90 40 90 Comparison 1 80 100 100 95 100 100 Number 1 2

This comparison shows that in the case of the 1-benzylpyrrolidin-2-one derivatives, the presence of a methyl substituent on the carbon in the ^ -position in the benzyl radical brings about a very significant improvement in herbicidal activity.

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

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In general, the compounds according to the invention, in particular when used in the course of crops and weeds, have a good herbicidal activity on grass weeds and a good selectivity towards crop plants such as maize, turnip, peanut, oilseed rape, cotton, bean, soya, litmus In the case of (D, L) -1- (2-methoxy- oC- methylbenzyl) -pyrrolidin-2-one (Compound 1), excellent results were obtained which, in the run at a dose of 2 kg / ha, were completely pinger grass, Millet, giant foxtail and foxtail have been destroyed and have a satisfactory herbicidal activity against wild oats and meadowweed, and this dose is well tolerated by the majority of the crops concerned. "

Excellent results were also obtained in the case of compound 1A, which consisted for the most part of the D (+) isomer of 1- (2-methoxy- [--methylbenzyl) -pyrrolidin-2-one and to a small extent the L (-) isomer of the same compound is ♦ ':

For the herbicidal B treatments by means of the compounds according to the invention, the dose of active material to be used may vary from 0.5 to 10 kg / ha, depending on the compound used, the type of crop and the nature of the soil Dose of CY / 1 and kg / ha ·

For practical use, the compounds of the present invention are rarely used alone. Most often, they are part of compositions which generally comprise, in addition to the active material of the present invention, a carrier and / or surfactant which are agriculturally useful and compatible with the active material »-

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The term "carrier" as used herein refers to an organic or mineral, natural or synthetic material with which the active material is associated in order to facilitate its application to the plant, on the grain or soil and its transport or handling · The carrier may be solid (tonics, natural or synthetic silicates, resins, waxes, solid fertilizers) or fluid (water, alcohols, ketones, petroleum fractions, chlorinated hydrocarbons, liquefied gases) ·

The surfactant may be an emulsifying, dispersing or wetting agent and ionic or nonionic. For example, the salts of polyacrylic acids, of ligninsulfonic acids, condensation products of ethylene oxide with fatty alcohols, fatty acids or fatty amines may be mentioned.

The compositions according to the invention can be prepared in the form of wettable powders, powders for dispersion or scattering, granules, solutions, emulsifiable concentrates, emulsions, concentrates in suspension and aerosols. -:

The wettable powders are usually prepared to contain from 20 to 95% by weight of the active substance and usually also contain a solid carrier, from 0 to 5% by weight of wetting agent, from 3 to 10% by weight. % of one or more stabilizers and / or other additives such as penetrants, adhesives or anticaking agents, dyes, etc. ·

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As an example, the following composition of a wettable powder is given:. active material (compound Kr. 1) 50 % calcium lignosulfate (deflocculant) 5% anionic wetting agent 1 % non-gelling silica 5 % kaolin (pulp) 39 %

The granules intended to be placed on the ground are usually made to have dimensions of between 0.1 and 2 mm. They may be produced by agglomeration or impregnation. In general, the granules will be 0.5 to 25% by weight of active material and 0 to 10% by weight of additives such as stabilizers, slow release modifiers , Binders and solvents.

The emulsifiable concentrates which are applicable by sputtering generally contain, apart from the solvent and, if necessary, a cosolvent 10 to 50 % w / w. to active material, 2 to 20 % w / v suitable additives such as stabilizers, penetrants, corrosion inhibitors and dyes and adhesives.

As an example, an emulsifiable concentrate is given below, the amounts being expressed in g / l: active material (compound ITr.1) 400 g / l alkali dodecylbenzenesulphonate 24 g / l

Konylphenol, oxyethylated with 10 moles of ethylene oxide 16 g / l cyclohexanone; 200 g / l

Fill aromatic solvent to 1 1

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The concentrates in suspension, which are also applicable to sputtering, are prepared in such a way that e ± a fluid stable product is obtained which does not settle out. They usually contain from 10 to 75% by weight of active material, 0.5 to 15 wt .-% of surface-active agent, from 0.1 to 10 percent by "-% thixotropic agents, 0 to 10 wt _e -% of suitable additives such as antifoams, corrosion inhibitors, stabilizers, penetrants and stickers, and as carrier, water or an organic liquid in the solid material is substantially insoluble. "Certain solid organic materials or mineral salts may be dissolved in the carrier to avoid sedimentation or as antigels to the water.

Aqueous dispersions and emulsions, for example compositions obtained by diluting a wettable powder or an emulsifiable concentrate according to the invention by means of water, also fall within the scope of the invention. The emulsions may be of the water-in oil or of the oil-in-oil type. Water and they may have a tough texture like that of a "mayonnaise". ,

The erfindungsgeinäßen compositions may contain protective colloids, adhesives or thickeners, thixotropic agents, stabilizers or sequestering agents other ingredients, for example, as well as other known active materials with pesticide properties, in particular insecticides or fungicides "

Claims (2)

Claim of invention . , A herbicidal composition for use in agriculture, characterized in that it contains as active material an effective amount of at least one pyrrolidin-2-one derivative of the general formula wherein the individual symbols have the following meanings: Ar is an ethenyl radical which is optionally substituted by 1 to 2 identical or different substituents which are selected from the halogen atoms, the alkyl radicals having 1 to 4 carbon atoms, the alkoxy radicals having 1 to 4 carbon atoms Alkenyloxy radicals having 2 to 4 carbon atoms, alkynyloxy radicals having 2 to 4 carbon atoms, hydroxyl, nitro, trifluoromethyl, monoalkylcarbamoyl having 1 to 4 carbon atoms in the alkyl part, dialkylcarbamoyl wherein each identical or different alkyl part has 1 to 4 carbon atoms, aliphatic acylamino having 2 to 5 Carbon atoms, or a radical Ar'-O-, wherein Ar 'is an optionally substituted phenyl radical or a heterocyclic radical having 6 chain members, optionally substituted and containing as hetero atoms an oxygen, sulfur or nitrogen atom; or Ar is an optionally substituted aromatic heterocyclic radical having 5 to 6 chain members and containing as heteroatom 1 to 2 identical or different atoms selected from nitrogen, oxygen or sulfur, R represents an alkyl radical 55 133 11 21 1 325 "- 25 - 1 to 4 carbon atoms, a cycloalkyl radical having 3 to 6 carbon atoms or an optionally substituted phenyl radical, in addition to a carrier or surface-active material .. 2. Composition according to item 1, characterized in that it contains 0.5 to 95 % by weight of active material. Method for selective weed control of maize, beet, peanut, rapeseed, cotton, bean, soy or litmus cultures, characterized in that a composition according to one of the items 1 and 2 is applied to these cultures or in their immediate vicinity or »applies.