DD234223A5 - HERBICIDES AND GROWTH-REGULATING AGENTS - Google Patents

Abstract

2-arylimidazolinones of the formula wherein A is O, S, NH or N-alkyl; B u. a. CN, a carboxylic ester carbothioester or carbonamide group; X is alkyl, Y is alkyl, cycloalkyl, alkenyl, alkynyl, phenyl or benzyl or X and Y together with C is a spiro-cycloalkyl group; ZH, (substituted alkyl, alkenyl, propargyl, an acyl, carbon ester or sulfoester group; n 1-3, R 1 -R 4 alkyl, alkoxy, alkoxycarbonyl, halogen, NO 2, CN, (substituted) phenoxy, (substituted) Phenyl, or any two adjacent -CHCH-CHCH- and R5 and R6 are H, alkyl or phenyl, are effective herbicides and growth regulators.

Description

A- (σ-4)

0.

applied, in which mean:

AO, S, NH or N (C ₁ -Cr-AIkYl);

B is -CN, -COOR ⁷ , -CONR ⁸ R ⁹ or COSR ¹⁰ ;

XC ₁ -C ₄ alkyl;

Y is d-Cr-alkyl, Cs-Cg-cycloalkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, phenyl or benzyl;

X and Y, together with the carbon atom to which they are attached, are an optionally substituted by -CH ₃ substituted C ₃ -Cg-spiro-cycloalkyl group;

Z is hydrogen, C ₁ -C ₄ -alkyl which may be substituted by C ₁ -C ₄ -alkoxy-carbonyl, C ₃ -C ₄ -alkenyl, propargyl, -CO-R ¹¹ or SO 2 -R ¹² ;

η is the numbers 1,2 or 3;

R ¹ , R ² , R ³ and R ⁴ independently of one another are hydrogen, C ₁ -C ₄ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkoxycarbonyl, halogen, nitro, cyano, phenoxy or phenyl, which may be combined with C ₁ -C ₄ -A ^- IkYl, C ₁ -C ₄ -alkoxy or halogen, and in each case two adjacent radicals R ^1, R ^2, R ³ or R ⁴ together the grouping -CH = CH-CH = CH- can form;

R ⁵ and R ⁶ independently of one another are hydrogen, (C ₁ -C ₄ -alkyl or phenyl;

R ^{7 is} hydrogen, CIC ₁ S-AIkYl, which optionally up to twice, but preferably with C ₁ -C ₄ -alkoxy, C! -C ₄ ) alkoxyethoxy, C ₃ -C ₅ -CyClOaIkYl, benzyloxy, phenyl, halogen , cyano, hydroxyl, oxiranyl, tetrahydrofuryl, (Ci-C ₄₎ alkylamino, (Ci-C ₄₎ dialkylamino, C ₁ -C ₄ -alkyl alkylthio, C ₁ -C ₄ -AIkYISuIfInYI ₁ C ₁ -C ₄ -AIkYlSuIfOnYl _{7 is} triazoyl or imidazolyl substituted; C ₁ -C ₆ -alkenyl, C ₁ -C ₄ -haloalkenyl, C ₁ -C ₆ -cycloalkyl, C ₁ -C 9 -cycloalkenyl, C ₃ -C ₆ -alkyl, benzyl, which may be substituted by chlorine or methyl in the benzene nucleus, phenyl, which may be with up to two Ci-C ₄ alkyl, nitro, halogen or methoxy groups may be substituted, or the group

-N = C »

R ^{8 is} hydrogen-iodo-Cr-alkyl;

R ^{9 is} hydrogen, C ₁ -C ₆ -alkyl, which is optionally substituted by a hydroxy group or a Ci-Cr-alkoxy group

is; C ₁ -C ₄ -alkyl-sulfonic or haloC-Ct-alkylsulfonyl; R ⁸ and R ⁹ together with the nitrogen atom, a 5- or 6-membered ring in which a carbon atom by oxygen

or nitrogen may be substituted and optionally substituted with up to two methyl groups; R ^{10 is} C ₁ -C ₅ -alkyl, phenyl or (C ₁ -C ₄ -alkoxycarbonyl) -Cr- and C ₁ -C ₄ -alkyl; R ^{11 is} C ₁ -C ₁₂ -alkyl which is optionally substituted with up to two C ₁ -C ₄ -alkoxy groups or with up to three halogen atoms; Phenyl, which may be substituted with up to two halogen atoms, a methyl, a nitro or a methoxy group; C ₁ -C ₄ -alkoxy, C ₃ -C ₇ -cycloalkyl, dC 1 -alkoxy-carbonyl, benzyloxy, phenoxy or -NR ¹⁵ R ¹⁶ ;

C ₁ -C ₄ alkyl, CF ₃ , CCI ₃ , phenyl, chlorophenyl or methylphenyl; and R ¹⁴ independently of one another are hydrogen, C ₁ -C ₄ -alkyl, C 1-6 -alkoxyalkyl, C ₃ -C ₆ -cycloalkyl or phenyl, or together with the carbon atom to which they are bonded, a C ₅ - or Cg- cycloalkyl; Hydrogen or C ₁ -C ₄ -alkyl, and C ₁ -C ₄ -alkyl, phenyl, chlorophenyl, methylphenyl, amino, mono- or di- (C ₁ -C ₄ -alkylamino

and their optical isomers (if X 4 = Y and / or R ⁵ Φ R ⁶ ) and their salts with acids and bases.

R ⁷ and R ^{11 are} in particular (C ₁ -C ₁₂ ) Alkyl, preferably (C ₁ -C ₄ ) AIlCyI.

The novel compounds of general formula 1 are obtained by reacting

a) amides of the formula 2

- COHH,

cyclized by dehydration or b) compounds of the formula 3

with at least equimolar amounts of the compounds of formula 4

and, if desired, the resulting compounds of formula 1 with Z = hydrogen by alkylation, acylation, sulfonation, oxidation, saponification, esterification or salt formation into other compounds of formula 1 are converted.

Re a): The cyclization of the amides may, for example, 2 with phosphorus pentachloride, advantageously in the presence of an unf ^"done reaction-inert solvent.

Examples include: toluene, xylene, chloroform or phosphorus oxychloride. The reaction temperature is not critical and can range from - 10 ⁰ C are varied and +150 ⁰ C. Reaction temperatures between 0 and 100 ^° C. are particularly advantageous.

The hydrochlorides of imidazolinone 1 are obtained in the first place. By conventional methods, e.g. by reaction with sodium carbonate or sodium bicarbonate, can be prepared from the free bases.

The cyclization can also be carried out in the presence of strong organic or inorganic acids, such as sulfuric acid, or p-toluenesulfonic acid, with simultaneous removal of the water formed at temperatures of ^{0 0} C to 150 ° C.

Particularly advantageously, the reaction can be carried out so that the water formed by acetylene distillation with a solvent such as toluene, xylene or chloroform, is separated. After neutralization, the products can be isolated by conventional methods.

Zub): The reaction can be carried out advantageously in the presence of an inert solvent such as toluene or chloroform, but also an excess of the reaction component 4 itself can serve as a solvent. The addition of an inorganic or inorganic base has an advantageous effect in many cases. The reaction temperature for this reaction is in the range between 0 ⁰ C and + 15O ⁰ C, advantageously between + 2O ⁰ C and 11O ⁰ C.

The reaction products of formula 1 where Z = hydrogen can be prepared in a simple manner by reaction with alkylating agents (methyl iodide, dimethyl sulfate) or acylating agents (acid chlorides) in the presence of bases or with isocyanates to give the compounds of formula 1 where Z = alkyl, Alkenyl, propargyl, -COR ¹¹ or -SO ₂ -R ¹² .

Compounds of the formula 1 in which R ⁷ is lower alkyl can also be converted into other compounds of the formula 1 by common processes, for example saponification, reaction, amidation.

The compounds of the invention, when Z is hydrogen, are tautomeric so that they may be present in either Formula 1 a / 1 b or as a mixture of 1 a and 1 b. These isomers also occur in the derivatives with Z Φ Η.

4 Ή / \ _v

1a

R-

The definitions of the formula 1 always include both isomeric structures of the formula 1 a and 1 b.

The acid addition salts of the compounds of the formula 1 or the salts with organic or inorganic bases are readily available in a generally known way. For salt formation on the one hand acids such as H ₂ SO ₄ , HCl, HNO ₃ or acetic acid, on the other bases such as NaOH, KOH, pyridine, trinthylamine, tri-hydroxyethylamine NH ₃ u. Like. Qualified.

The amides of the formula 2 can be easily obtained from the aminoamides 5 and the correspondingly substituted carboxylic acid derivatives 6. Suitable derivatives are, for. As acid chlorides or carbonic acid alkyl esters (R ¹⁷ = Cl, -0-COOAalkyl).

Compounds of the formula 3 are accessible by the process given in DE-OS 2,700,270.

If unsymmetrically substituted phthalic anhydrides are used as starting materials for the synthesis of the compounds of formula 1, positional isomers can occur both in the amides as formula 2 and in the compounds of formula 3 which can be used in process variants a) and b). As a result, then the compounds of formula 1 as a mixture of two position isomers (1 c, 1 d) are present, wherein 1 c then corresponds to the formula 1 and at 1 d, the two right-hand substituents of formula 1 are reversed, so that the imidazolionone -rest is directly adjacent to the substituent R1.

The present compounds according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even hard-to-combat perennial root weeds are well detected by the active ingredients. It does not matter whether the substances are applied in pre-sowing, pre-emergence or post-emergence spraying. If the compounds according to the invention are applied to the surface of the earth before germination, the emergence of the seedlings is not completely prevented. The weeds grow to the cotyledon stage but then stop growing and finally die off after 3 weeks.

Upon application of the active ingredients to the green parts of the plants postemergence also occurs very quickly after treatment, a drastic halt in growth and the weed plants remain in the existing stage of application growth stage or die after a period of time completely, so that in this way one for the crops harmful weed competition can be eliminated very early and sustainably by the use of the novel agents of the invention. Although the compounds of the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops such. As wheat, barley, rye, rice, corn, sugar beet, cotton and soy only insignificant or not damaged. The substances according to the invention thus have an excellent selectivity in crop plants and, for these reasons, are very suitable for controlling unwanted plant growth in agricultural crops.

In addition, they have growth-regulatory properties in crop plants. They regulate into the plant's metabolism and can thus be used to facilitate harvesting such as. B. by triggering desiccation, abscission and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures as it reduces or completely eliminates storage

The compositions according to the invention can be used as wettable powders, emulsifiable concentrates, sprayable solutions, dusts, mordants, dispersions, granules or microgranules in the customary formulations.

Injectable powders are preparations which are uniformly dispersible in water and which, in addition to the active ingredient, may also contain wetting agent, except, if appropriate, a diluent or inert substance. Polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenylsulfonates and dispersants, e.g. lignosulfonic acid sodium, 2,2'-di-naphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or oleoylmethyltaurine acid. The preparation is carried out in customary, e.g. by grinding and mixing the components.

Emulsifiable concentrates may e.g. by dissolving the active ingredient in an inert organic solvent, e.g.

Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. In the case of liquid active substances, the solvent content may also be omitted in whole or in part. Examples of emulsifiers which may be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, fatty alcohol / propylene oxide / ethylene oxide condensation products, alkyl polyglycol ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusts can be obtained by grinding the active ingredient with finely divided, solid substances, eg. Talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.

Granules can either be prepared by atomizing the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrations by means of binders, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils on the surface of carriers such as sand, kaolinites or granulated inert material.

Also, suitable active ingredients may be typically granulated in the form of fertilizer granules, if desired in admixture with fertilizers.

In wettable powders, the drug concentration is e.g. about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation constituents. For emulsifiable concentrates, the active ingredient concentration may be about 10 to 80% by weight.

Dusty formulations usually contain from 5% to 20% by weight of active ingredient, sprayable solutions from about 2% to 20% by weight.

In the case of granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.

In addition, the named active substance formulations optionally contain the usual ones! ! AFT. Wetting, dispersing, emulsifying, penetrating, solvents, fillers or carriers.

For use, the present in commercial form concentrates are optionally diluted in a conventional manner, for. B.

for wettable powders, emulsifiable concentrates, dispersions and sometimes also for microgranules by means of water.

Dusty and granulated preparations and sprayable solutions are usually no longer diluted with other inert substances before use.

The application rates of active ingredient of the formula I vary depending on the indication between 0.01 to 10 kg of active ingredient.

Also, mixtures or blends with other agents, e.g. Insecticides, acarides, herbicides, fertilizers, growth regulators or fungicides may be possible.

Below are some formulation examples listed:

A dust is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc or inert material and comminuting in a hammer mill.

A wettable powder easily dispersible in water is obtained by mixing 25 parts by weight of active ingredient, 64 parts by weight of kaolin-containing quartz as an inert, 10 parts by weight of potassium lignosulfonate and 1 part by weight of oleoylmethyltaurine sodium as a wetting and dispersing agent, and grinding in a pin mill.

A dispersion concentrate readily dispersible in water is obtained by mixing 20 parts by weight of active compound with 6 parts by weight of alkylphenol polyglycol ether (Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 AeO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 225 to over 377 ° C.) a ball mill to a fineness of less than 5 microns milled.

An emulsifiable concentrate is obtained from 15 parts by weight of active compound, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol (10 AeO) as emulsifier.

embodiment

The following examples serve to further illustrate the invention: A. Preparation Examples Example 1 (starting material) 2- (1-Methoxycarbonyl) -ethoxycarbonyl-benzoic acid IM-2- (2-carbamoyl-3-methyl) -butylamide To a mixture of 23 , 3g (0.18 mol) of 2-methylvalinamide, 21.7 g of triethylamine and 150 ml of methylene chloride are added dropwise at 0 to 10 ⁰ C 48.4 g (0.18 mol) of 2- (1-methoxycarbonyl) -ethoxycarbonyl-benzoylchloridzu. The mixture is stirred at room temperature for 1 h, the reaction mixture is washed twice with 100 ml of water, the organic phase is dried over sodium sulfate and concentrated by evaporation: 50.1 g (81% of theory) of 2- (1-methoxycarbonyl) -ethoxycarbonylbenzoic acid N-2 - (2-carbamoyl-3-methyl) -butylamide, a colorless

¹ H-NMR (60MHz, CDCl ₃ ) δ = 1.00 (d, J = 7Hz, 6H, -CH- (CH ₃ I ₂ ), 1.60 (s, 3H, CH ₃ ), 1.64 ( d, J = 7Hz, 3H, CH-CH _3), 2.2 (h, J = 7Hz,

1H, -CH- (CHs) ₂ ); 3.83 (s, 3H, OCH ₃ ); 5.43 (q, J = 7 Hz, 1H, CH-CH _3); 6.8-8.3 ppm (m, 7H, Ph, NH,

NH ₂ ),

Example 2

5-Isopropyl-2- (2- (1-methoxycarbonyl) ethoxycarbonylphenyl) -5-methyl-4-oxo-2-imidazoline To a solution of 42.8 g (0.12 mol) of 2- (1-methoxycarbonyl) -ethoxycarbonyl Benzoic acid N-2- (2-carbamoyl-3-methyl) -butylamid in 50 ml of phosphorus oxychloride are added at room temperature 27.05 g (0.13 mol) of phosphorus pentachloride, stirred for 2 h at room temperature after evaporation in vacuo and hydrolyzed with 300g of ice cream. After neutralization with sodium bicarbonate is extracted twice with ethyl acetate, dried over sodium sulfate and evaporated. This gives 34.3 g (84% of theory) of 5-isopropyl-2- (2- {1-methoxycarbonyl) -ethoxycarbonyl-phenyl) -5-methyl-4-oxo-2-imidazoline, a light pale yellow oil

¹ H-NMR (CDCI _3, 50 MHz) δ = 0,90,1,05 (2d, J = 7 Hz, 6H, CH- (CH ₃ I _2); 1.37 (s, 3H, CH ₃₎ 1.57 (d, J = 7 Hz, 3H, CH-CH _3), 2.1 (h,

J = 7Hz), 1H, CH- (CHa) ₂ ); 3.73 (s, 3H, OCH ₃ , 5.23 (q, J = 7Hz, 1H, -CH-CH ₃ ), 7.1-8.1 ppm (m, 5H,

Ph, NH).

Example 3

1-Acetyl-5-isopropyl-2- (2- {1-methoxycarbonyl) -ethoxycarbonyl-phenyl) -5-methyl-4-oxo-2-imidazoline A mixture of 8.9 g (0.026 mol) of 5-isopropyl-2 ( 2- (1-methoxycarbonyl) -ethoxycarbonylphenyl) -5-methyl-4-oxo-2-imidazoline, 15 g of acetic anhydride and 50 ml of abs. Toluene are heated to 80 ⁰ C for 2 h. After cooling, the mixture is poured onto 200 g of ice, the organic phase separated, dried and purified by chromatography (silica gel, LM petroleum ether - ethyl acetate 7: 3). This gives 6.9 g (69% of theory) of 1-acetyl-5-isopropyl-2- (2- (1-methoxycarbonyl) ethoxycarbonylphenyl) -5-methyl-4-oxo-2-imidazoline, a colorless oil

¹ H-NMR (60 MHz, CDCl ₃ ) δ = 0.97, 1.10 (2d, J = 7 Hz, 6H, CH- (CH ₃ ) ₂ ); 1.43 (s, 3H, CH _3); 1.56 (d, J = 7Hz, 3H, _-CH-CH3); 2.1 (h,

J = 7Hz, 1H, CH- (CH ₃ J ₂ ); 2.45 (sa, 3H, -COCH ₃ ); 3.67 (s, 3H, OCH ₃ ); 5.2 (q, J = 7Hz, 1H, CH-CH _3);

7.3-8.3ppm (4H, Ph)

 Further examples are listed in Table 1.

Table 1

R '

Example no.

R ¹

R ⁴

H H H H H H H H H H

H H H H H H H H H H

H H H

Cl

CH ₃

H H H

H H H H H H H H H H

H H

HH HH HH CH ₃ H

CH ₃ CH (CH ₃ J ₂ CH ₃ H CH ₃ H CH ₃ H CH ₃ H CH ₃ H CH ₃ H

H CH ₃ HH CH ₃ HH CH ₃ H

H CH ₃ H

19 H H H H CH ₃ H H CH ₃ H 20 H H H H CH ₃ H H CH ₃ CH ₃ 21 H H H H CH ₃ H H CH ₃ H 22 H H H H CH ₃ H H CH ₃ H 23 H H H H CH ₃ H H CH ₃ H 24 H H H H CH ₃ H H CH ₃ H 25 -CH = CH-CH = CH-H CH ₃ H H CH ₃ H 26 -CH = CH-CH = Ch-H CH ₃ H H CH ₃ H 27 H CH ₃ H H H H 28 H CH ₃ H H H H 29 H CH ₃ H H H H 30 H CH ₃ H H H H 31 H CH ₃ H H H H 32 H CH ₃ H H H H 33 H CH ₃ H H H H 34 H CH ₃ H H H H 35 H H H CH ₃ H H 36 H H H CH ₃ H H 37 H H H CH ₃ H H 38 H Cl Cl H H H · 39 H Cl Cl H H H 40 H Cl Cl H H H 41 H Cl CH ₃ H H CH ₃ 42 H Cl CH ₃ H H CH ₃ 43 H The compounds 27 to 40, CH ₃ H 44 H 1 b) CH ₃ H 45 H CH ₃ H 46 H CH ₃ H 47 H CH ₃ H 48 H CH ₃ H 49 H CH ₃ H 50 H CH ₃ H 43 to 45

1 O COOCH ₃ H CH ₃ CH (CH ₃ J ₂ CH ₃ CH ₃ 1 O COOH H CH ₃ C ₂ H ₅ CH ₂ -CH (CH ₃ ) ;, 1 S COOCH ₃ H CH ₃ CH (CH ₃ J ₂ CH (CH ₃ IC ₂ H ₅ 1 O CN H CH ₃ CH (CH ₃ J ₂ CH (CHs) -C ₂ H ₅ 1 NH CONH ₂ H CH ₃ CH (CH ₃ I ₂ CH (CH ₃ JC ₂ H ₅ 1 O COOCH ₃ -CO-phenyl CH ₃ CH (CH ₃ ) ₂ CH (CHs) ₂ 1 O COOCH ₃ H CH ₃ CH (CHs) ₂ CH (CH ₃ J ₂ 1 O COOCH ₃ H CH ₃ CH (CHs) ₂ CH (CHs) ₂ 1 O COOC ₂ H ₅ H CH ₃ C ₂ H ₅ CH (CH ₃ J ₂ 1 O COOC ₂ H ₅ H CH ₃ CH (CH ₃ J ₂ CH (CH ₃ J ₂ 1 O COOC ₂ H ₅ H CH ₃ CH (CH ₃ J ₂ CH (CH ₃ J ₂ 1 O COOC ₂ H ₅ -COOCH ₃ CH ₃ CH (CH ₃ J ₂ ) CH (CHs) ₂ 1 O COOC ₂ H ₅ -CONHCH ₃ CH ₃ CH (CH ₃ I ₂ CH (CH ₃ J ₂ 1 O COOC ₂ H ₅ O CH ₃ CH (CHs) ₂ ) CH (CH ₃ ), 1 O COOC ₂ H ₅ O H -CH ₂ -CH ₂ -CH ₂ -CH ₂ -CH- CH (CH ₃ I ₂ CH (CH ₃ J ₂ 1 O COOC ₂ H ₅ -COCH (CH ₃ J ₂ CH (CH ₃ J ₂ 1 O CN H CH ₃ CH (CH ₃ J ₂ 1 O COOC ₂ H ₅ H CH ₃ CH (CH ₃ J ₇ 1 O COOC ₂ H ₅ H CH ₃ CH (CH ₃ J ₂ 1 O COOC ₂ H ₅ -COOCH ₃ CH ₃ CH (CH ₃ J ₂ 1 O COOC ₂ H ₅ -CONHCH ₃ CH ₃ CH (CH ₃ J ₂ 1 O COOCH ₃ H CH ₃ CH (CH ₃ J ₂ 1 O COOCH ₃ -CONHCH ₃ CH ₃ CH (CH ₃ J ₂ 1 O COOCH ₃ H CH ₃ CH (CH ₃ J ₂ 1 O COOCH ₃ COCH ₃ CH ₃ CH (CH ₃ J ₂ 1 O COOCH ₃ COOCH ₃ CH ₃ CH (CH ₃ J ₂ 1 O COOCH ₃ COCOOCH ₃ CH ₃ CH (CH ₃ J ₂ 1 O COOCH ₃ CONHCH ₃ CH ₃ CH (CH ₃ J ₂ 1 O COOCH ₃ CONH-phenyl Ch ₃ cyclopropyl 1 O COOCH ₃ CH ₃ CH ₃ cyclopropyl 1 O COOCH ₃ CCOCHz-phenyl CH ₃ 1 O COOC ₂ H ₅ COCH ₃ CH ₃ 1 O COOC ₂ H ₅ COOCH ₃ CH ₃ 1 O COOC ₂ H ₅ CONHCH ₃ CH ₃ 1 O COOC ₂ H ₅ CH ₂ -COOCH ₃ CH ₃ 1 O COOC ₂ H ₅ CONHNH ₂ CH ₃ 1 O COOC ₂ H ₅ CONHN (CH ₃ J ₂ CH ₃ 1 O COOC ₂ H ₅ H CH ₃ 1 O COOC ₂ H ₅ COCOOC ₃ H ₇ CH ₃ 1 O COOC ₂ H ₅ H CH ₃ 1 O COOC ₂ H ₅ CONHCH ₃ CH ₃ 1 O COOC ₂ H ₅ COOC ₄ H ₉ CH ₃ 1 O COOC ₂ H ₅ H CH ₃ 1 O COOC ₂ H ₅ COCH ₃ CH ₃ 1 O COOC ₂ H ₅ COCOOCHs CH ₃ 1 O COOCH ₃ H CH ₃ 1 O COOCH ₃ CONH-phenyl CH ₃

(hydro

chloride)

Oil Oil Oil Oil Oil Oil Oil Oil Oil Oil Oil Oil Oil Oil Oil Oil Ol Oil Oil Oil Oil Oil Oil Oil

49 and 50 are in each case as a mixture of the structural isomers according to p. 8 (Formulas 1 a and

t. Biological examples for herbicidal action

) Damage to weed plants or crop tolerance was scored in a 0-5 key. ) abei means: ι = without effect (damage) = 0-20% effect! = 20-40% effect! = 40-60% effect l * = 60-80% effect j = 80-100% effect

I. Action against weeds

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in clay soil in plastic pots (0 9cm) and covered with soil. The formulated as wettable powders or as emulsion concentrates compounds of the invention ^were: orm of aqueous suspensions or emulsions pool on the Erdorberf applied. The amount of water used per pot was equivalent to labet 600 l / ha. After the treatment, the test pots were placed in the greenhouse and the cultivated plants were cultivated under good growth conditions (temperature: 23 ± 1 ° C., relative humidity 60 to 80%). After approx.

For 3 weeks, the damage to the plant was assessed visually. As a comparison, untreated controls were used.

As can be seen from the values in Table 2, the compounds according to the invention have, in the pre-emergence process, an excellent herbicidal activity against economically important monocotyledonous and dicotyledonous harmful plants.

Similarly, various weeds are grown in pots in the greenhouse to the 3 to 6 leaf stage and then postemergence treated with the compounds of the present invention (formulated as a wettable powder). 4 weeks later, the test plants were compared vis-à-vis untreated control plant η visually, by the injury

was estimated.

The results of the experiment (Table 3) prove the good herbicidal properties of the compounds.

Table 2

Pre-emergence herbicidal efficacy (% injury)

Example kg AS ALM POA AMR SIA TAW GS

No. / ha

2 2.4 5 5 5 5 5 5 3 2.4 5 5 5 5 5 5 4 2.4 5 5 5 5 5 5 · 9 2.4 5 4 5 5 5 5 10 2.4 5 5 5 5 - - 12 2.4 5 5 5 5 4 5 13 2.4 5 5 5 5 5 5 14 2.4 5 5 5 5 5 5 15 2.4 5 5 5 5 4 4 16 2.4 5 5 5 5 5 5 25 2.4 5 5 5 5 - - 26 2.4 4 - 5 5 - - 27 2.4 5 5 5 5 5 4 31 2.4 "" 5 5 5 5 - -

Table 2 (continued) Pre-emergence herbicidal efficacy (% injury)

Example no.

kg AS

/Ha

LOM

ECG

STM

SIA

28 2.4

29 2.4

35 2.4

36 2.4

37 2.4

ALM = Alopecurus myosuroides POA = Poa annua AMR = Amaranthus retroflexus SIA = Sinapisalba TAW = Triticum aestivum (winter) GS = Glycine soya LOM = Lolium multiflorum ECG = Echinochloa crus-galli STM = Stellaria media

5 5 5 4 4

5 5

 5 4 5

5 5 5 5 5

Table 3

Post-emergence herbicidal efficacy (% injury)

Example kgAS / ha ALM POA AMR SIA LOM ECG STM

2 2.4 -   - 5 5 4 2.4 5 4 5 5 - - - 10 2.4 4 - 5 5 - - - 12 2.4 - - 5 4 - - - 14 2.4 - - 5 5 - - - 16 2.4 - - 5 5 - - - 27 2.4 5 4 5 5 - - - 28 2.4 5 5 5 5 - - - 29 2.4 - - - 5 5 5 5 31 2.4 - - 5 5 - - - 35 2.4 - - - 5 5 5 5 36 2.4 - - - 5 4 - 4 37 2.4 - - 4

Check for growth-regulating effect

1. Growth inhibition in cereals

In shell experiments in the greenhouse young cereal plants (wheat, barley and rye) in the 3-leaf stage with the compounds to be tested were sprayed dripping wet. After the untreated control plants had reached a stature height of about 55 cm, the growth was measured in all plants and the growth inhibition in% of the growth of the control plants was calculated. In addition, the phytotoxic effect of the compounds was observed. The compounds proved to be very effective.

2. Growth inhibition on bush beans

10 to 15cm bush beans were sprayed dripping wet with the active ingredient preparations. After 2 weeks, the growth was measured and the growth inhibition in% of the growth of the control plants was calculated. The compounds proved to be very effective.

Claims (2)

Invention claim: 1. herbicidal and growth-regulating center !, characterized in that they are active ingredient imidazolinones of the formula r4 // / N in which mean: AO, S, NH or N (C ₁ -C ₆ -AIM); B is -CN, -COOR ⁷ , -CONR ⁸ R ⁹ or COSR ¹⁰ ; XC ₁ -C ₄ alkyl; Y is C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkylene, phenyl or benzyl; X and Y, together with the carbon atom to which they are bonded, are an optionally substituted by -CH ₃ substituted C ₃ -C ₆ -sipro-cycloalkyl group; Z is hydrogen, C ₁ -C ₄ -alkyl which may be substituted by C ₁ -C ₄ -alkoxy-carbonyl, Q ₁ -C ₄ -alkenyl, propargyl, -CO-R "or SO ₂ -R ¹² ; η is the numbers 1,2 or 3; R ¹ , R ² , R ³ and R ⁴ independently of one another are hydrogen, C ₁ -C ₄ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkoxycarbonyl, halogen, nitro, cyano, phenoxy or phenyl, which may be combined with C ₁ -C ₄ -alkyl, Ci-C ₄ -alkoxy or halogen, and in each case two adjacent radicals R ^1, R ² R ³ or R ⁴ together the grouping -CH = CH-CH CH-can form =; R ⁵ and R ^{6 are} independently hydrogen, (C ₁ -C ₄ -alkyl or phenyl; R ^{7 is} hydrogen, C ₁ -C ₂ -alkyl, which is optionally up to twice, but preferably monosubstituted, by C ₁ -C ₄ -alkoxy, (C ₁ -C ₄ ) -alkoxyethoxy, C ₃ -C ₆ -cycloalkyl, benzyloxy, phenyl , Halogen, cyano, hydroxyl, oxiranyl, tetrahydrofuryl, (C ₁ -C ₄ ) -alkylamino, (C ₁ -C ₄ ) -dialkylamino, C ₁ -C ₄ -alkyl- ₁ -one, CH ₄ -alkylsulfinyl, C ₁ -alkylsulfonyl, triazolyl or imidazolyl is; C ₁ -C ₆ alkenyl, C ₁ -C ₆ -cycloalkenyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C 12 -cycloalkenyl, C ₃ -C ₆ -alkyl, benzyl, which may optionally be substituted by chlorine or methyl in the benzene nucleus, phenyl, which may optionally contain up to two C 1 -C ₄ -alkyl,
Nitro, halogen or methoxy substituted
can be, or the group ^N 14. R ^{8 is} hydrogen or C 1 -C ₄ -alkyl; R ^{9 is} hydrogen, C ₁ -C ₆ -alkyl, which is optionally substituted by a hydroxy group or a C ₁ -C ₃ -alkoxy GtUpPe; Ci-Cj-alkylsulfonyl or halo gen-C ^ d-alkylsulfonyl;
R ⁸ and R ⁹ together with the nitrogen atom of a 5- or 6-membered ring in which a carbon atom may be replaced by oxygen or nitrogen and the optionally substituted with up to two methyl groups;
R ^{10 is} C ₁ -C ₆ -alkyl, phenyl or (C ₁ -C ₆ -alkoxycarbonyo-C ₁ - and C ₂ -alkyl; R ^{11 is} C ₁ -C 12 -alkyl, which may be reacted with up to two dd-alkoxy groups or with up to three halogen atoms is substituted; Phenyl, which may be substituted with up to two halogen atoms, a methyl, a nitro or a methoxy group; C ₁ -C ₄ -alkoxy, Qr-Cy-cycloalkyl, C ₁ -C ₄ -alkoxy-CaTbOnYl, benzyloxy, phenoxy or -NR ¹⁵ R ¹⁶ ; R ^{12 is} C ₁ -C ₄ alkyl, CF ₃ , CCI ₃ , phenyl, chlorophenyl or methylphenyl;
R ¹³ and R ¹⁴ independently of one another are hydrogen, C ₁ -C ₄ -alkyl, dd-alkoxyalkyl, C ₃ -C ₆ -cycloalkyl or phenyl, or together with the carbon atom to which they are attached, a C ₅ - or Ce-cycloalkyl group, R ^{15 is} hydrogen or C ₁ -C ₄ -AlkYl, and
R ^{16 is} C ₁ -C ₄ -alkyl, phenyl, chlorophenyl, methylphenyl, amino, mono- or di-iCi-Q-alkylamino and their optical isomers (if X = Y and / or R ⁵ = R ⁶ ) and their salts with Acids and bases in addition to customary formulation auxiliaries. 2. Use of the agents according to item 1, characterized in that they are used as herbicidal and growth regulators. -. !. A method for controlling unwanted plants or for growth regulation, characterized in that applying an effective amount of a compound of formula 1 according to item 1 on the treatment area or plants to be treated. Field of application of the invention The invention relates to herbicidal and growth-regulating agents for use in agriculture. Characteristic of the known technical solutions There is no information as to whether imidazolinones are already used as herbicidal and growth-regulating compounds. Object of the invention The aim of the invention is to provide novel agents having herbicidal and growth-regulating properties which can be used in crop-culture crops to control undesired plant growth and to regulate plant growth. Explanation of the essence of the invention The invention has for its object to find new compounds with the desired properties, which are suitable as active ingredient in herbicidal and growth-regulating agents. According to the invention as the active ingredient new, herbicidally active 2-aryl-substituted imidazolinones of the formula. 1