DD283318A5 - HERBICIDE MEDIUM - Google Patents

Abstract

The invention relates to herbicidal compositions containing an effective amount of novel Phenoxyphenylessigsaeurederivate or their salts or stereoisomers in conjunction with conventional adjuvants for crop protection formulations. According to the invention, the novel agents contain as active ingredient 3-phenoxy-phenylacetic acid derivatives of the formula ## STR1 ## in which X, Y and R.sup.1 have the meaning given in the description and in the claims. Formula (I) {active substance new 3-phenoxy-phenylacetic acid derivatives; strong herbicidal action; suitable for selective weed control in crops}

Description

CH ₂ -COOH

or reacting their esters or acid halides with a compound of the formula Y-H and, if appropriate, converting the compounds obtained into their salts.

4. The method according to claim 3, characterized in that after

a) is reacted with a nitrating agent from the group nitric acid, nitrogen oxides and nitrates and in the presence of sulfuric acid, acetic anhydride, glacial acetic acid or a cosolvent such as dichloromethane.

5. The method according to claim 4, characterized in that in addition in the presence of a catalyst such as boron trifluoride etherate, trifluoroacetic acid, methanesulfonic acid, trifluoroacetic anhydride or a metal salt from the series of thallium (I), copper (I) and copper (II) is reacted.

6. A method for controlling undesirable plants, characterized in that applied to these or the effective areas an effective amount of a compound of formula I of claims or 2 or their salts or stereoisomers.

Field of application of the invention

The invention relates to herbicidal compositions containing novel 3-phenoxy-phenylacetic acid derivatives, to a process for the preparation of these compounds and to their use for selective weed control in crops of useful plants,

Characteristic of the known state of the art

It is already known that substituted Phenoxyphenylessigsäurederivate have herbicidal properties, see JΡΑ 62072-647 and EP-A 161529. However, these have disadvantages in the application, such as. As insufficient selectivity or too low activity against important schwekekämpfbare harmful plants.

Object of the invention

The aim of the invention is the provision of new agents with strong herbicidal activity, which are suitable for selective weed control in crops.

Explanation of the essence of the invention

The invention has for its object to find new compounds which are suitable as active ingredient in herbicidal compositions having the desired properties.

There have now been found new Phenoxyphenylessigsäurederivate, which surprisingly an advantageous selective. Have a herbicidal action and act against a wide range of anti-fouling weeds.

The present invention therefore relates to compounds of the formula I, their salts and stereoisomers

01

X halogen,

Y a rust of formulas NR ² R ³ or W- (GR ² R ⁴ ) _n -CZR ⁵ ,

W O or S,

Z O.S or NR ¹ ,

η 1,2,3 or 4,

R ^1, R ⁴ are independently hydrogen, (C, -C ₄₎ alkyl, (C ₁ -C ₄₎ -alkoxy or halo (C, -C ₄₎ alkyl,

R ² , R ³ are each independently hydrogen, (C) -C ₄ ) alkyl which is mono- or polysubstituted by halogen and / or mono- to disubstituted by cyano, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) AIkVUhJo, di (C ₁ -C ₄ ) alkylamino, carboxy, (C ₁ -C ₄ ) alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₄ -alkylaminocarbonyl.DilC, C ₁ -C ₄ ) alkylaminocarbonyl, tri-C ₁ -C ₄ -alkyhilyl, unsubstituted or by (C ₁ -C ₄ ) -alkyl. C ₄ ) AlkVl, (C ₁ -C ₄ ) alkoxy or halogen substituted phenyl, furanyl or thienyl may be substituted, (Cr-CeJAIkenyl, (C ₂ -C ₆ ) alkynyl, (Ct-C-alkoxycarbonyl, phenyl, by (C, -C ₄ ) alkyl, halogen, cyano or (C ₁ -C ₄ ) alkoxy, or (C ₁ -C ₄ ) alkoxy and

R ⁵ is hydrogen, (C ₁ -C ₆₎ -alkyl which is mono- or polysubstituted by halogen and / or monosubstituted or disubstituted by nitro, cyano, (C ₁ -C ₄₎ -alkoxy, (Ci-C ₄₎ alkylthio, tri (C, -C ₄ ) alkylsilyl, unsubstituted or by (C, -C ₄ ) alkyl, (C, -C ₄ ) alkoxy or halogen-substituted phenyl, furanyl or thienyl may be substituted, further (C ₂ -C ₆ ) alkenyl , (C? -Ce) alkynyl, (Cs-C ₇ ) cycloalkyl, phenyl which may be substituted by (C ₁ -C ₄ ) Al kVl, (C ₁ -C ₄ ) alkoxy, halogen or cyano, or in the case of Z = NR ^{1 is} a radical (C ₁ -C ₄ ) AIkOXy

means.

Preferred of the compounds of formula I are those in which

O γ-W- (CR ² R ⁴ ) _n -CZR ⁵ ,

W O or S,

Z O.S or NR ¹

R ^{1 is} H or CH ₃ ,

R ^{2 is} H or (C, -C ₄ ) alkyl, R ^{4 is} H, (C ₁ -C ₄ ) alkyl, which may be substituted by halogen, (C ₁ -C ₄ ) alkoxy or benzyl and R ^{5 has} the abovementioned meanings.

Alkyl may be straight-chain or branched in the above definitions. Halogen is in particular fluorine, chlorine or bromine. In the case of R ⁵ = hydrogen or R ² or R ³ = alkyl by carboxyl subctituiertes the compounds of formula I can be present as salts, with those salts which are applicable for agriculture come used. Suitable agricultural salts for the compounds of the formula I are, for example: Na, K, Mg, Ca, Zn salts or ammonium or organic mono- to tetra-substituted ammonium, sulfonium, sulfoxonium or Phosphonium salts, wherein as organic radicals usual substituents such as alkyl, hydroxyalkyl, cycloalkyl or optionally substituted phenyl radicals come into question

 The compounds of the formula I have in the groupings

O O

-CHR ^ -CY for the case R ¹ * H and W- (CR ² R ⁴ ) _n -C-ZR ⁵ for the

Case R ² Φ R ⁴ and optionally in the radicals R'-R ⁶ itself optically active centers. They can therefore be present as stereoisomer mixtures or in the form of pure stereoisomer mixtures or in the form of pure stereoisomers. These are also encompassed by the present invention.

The present invention also provides processes for the preparation of the compounds of formula I and their salts, characterized in that a) a compound of formula II

(II)

CH-C-Y

by reaction with a nitrating agent, preferably nitric acid, nitrogen oxides or nitrates, or b) for R ¹ = H, a compound of formula III

(III)

CH ₂ -COOH

or deron ester or acid halide with a compound of formula Y-H and reacting the resulting compounds, if appropriate, converted into their salts.

The process (a) may optionally be carried out in the presence of sulfuric acid, acetic anhydride, glacial acetic acid or a cosolvent such as Dichloromethane optionally with the addition of a catalyst such as boron trifluoride etherate, trifluoroacetic acid, Methanesulfonic acid, trifluoroacetic anhydride or a Metallse.lzes such. Thallium (I), copper (I) or copper (II)

be performed.

In the case of variant (b), the acid derivatives such as esters and acid chlorides may be used instead of the compounds known per se

of formula III (JP-A 62072-647) are used. As esters in particular alkyl esters such as methyl or ethyl esters in

consideration; In particular, acid chlorides can be used as the acid halides. The production of esters and Acid halide b is carried out by customary methods. The implementation of process (b) is carried out according to known per se Methods (see, for example, Houben-Weyl, Bd.VIII, p.503ff., And p.647ff. [1952]). The compounds of the formula II can be prepared from the compounds of the formula IV

.cl

-3-O-0-O

(IV)

CH-C-OH II

)1

or their acid derivatives, such as esters or halides, by the methods mentioned for process (b).

The compounds of formula IV are known for R ¹ = H (JP-A 62072-647). The other compounds of formula IV are on

analogous way.

If the preparation of the compounds I or II is based on an acid chloride, this can be done during the reaction

liberated HCI gas by an inert gas or by binding with a tert. Remove amine, metal hydroxide or metal carbonate.

The compounds of the invention have excellent herbicidal activity against a broad spectrum

economically important monocotyledonous and dicotyledonous harmful plants. Also difficult to combat perennial weeds that off

Rhizomes, Wurzelstöckchen or other permanent organs drive out, are well detected by the active ingredients. examples for

such harmful plants are various species of Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria,

Cyperus, Agropyron, Cynodon, Imperata, Sorghum, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon, Sida, Convolvulus, Cirsium, Rumex, Artemisia, Sagittarir., Alisma, Eleocharis and Scirpus. That's it

regardless of whether the substances are applied in the pre-sowing, pre-emergence or postemergence process.

When the compounds of the invention are applied to the soil surface prior to germination, either agglomeration will occur

weed seedlings are completely prevented, or the weeds grow to the cotyledon stage, but then cease to grow and eventually die off after three to four weeks. Upon application of the active ingredients to the green parts of the plants postemergence also occurs very quickly after treatment drastic

Stop growth, and the weed plants remain in the existing at the time of application growth stage

or die off more or less rapidly after a certain time, so that in this way eir.o can be eliminated very early and sustainably for the crop damage weed competition by the Einsau the new compounds of the invention.

Although the compounds of the invention have excellent herbicidal activity over mono- and dicots Weeds, crops of economically important crops such. Wheat, barley, rye, rice, corn, Sugarbeet, cotton and soy only negligibly or not at all damaged. The present compounds are useful

These reasons are very good for selective control of undesirable plant growth in agricultural

Plantations. The compositions of the invention can be used as wettable powders, emulsifiable concentrates, sprayable solutions, dusts, Beizmittel, dispersions, granules or microgranules are used in the usual preparations. Injection powders are preparations which are uniformly dispersible in water and contain, in addition to the active substance, if appropriate, one Diluent or inert or wetting agent, z. As polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or Alkylphenylsulfonates and dispersants, e.g. Sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid Sodium, dibutylnaphthalenesulfonate sodium or oleoylmethyltaurine acid. The production

takes place in the usual way, for. B. by grinding and mixing of the components.

Emulsifiable concentrates may, for. B. by dissolving the active ingredient in an inert organic solvent, for. B. butanol, Cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of

one or more emulsifiers are produced. In the case of liquid active substances, the proportion of solvent can also be omitted completely or partially. As emulsifiers can be used, for example:

Alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, Aikyl-aryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, fatty alcohol Propylene oxide-ethylene oxide condensation product, alkyl polyglycol ether, sorbitan fatty acid ester, Polyoxethylenesorb'tanfettsäureester or Polyoxethylenensorbitester. Dusts can be obtained by grinding the active substance with finely divided, solid substances z. As talc, natural clays like Kaolin, bentonite, pyrophilite or diatomaceous earth obtained. Granules can be prepared either by spraying the active ingredient onto adsorptive, granulated inert material

or by applying Wirkstoffkonzentrationsn means of binders, for. As polyvinyl alcohol, polyacrylsaurem

Sodium or mineral oils on the surface of carriers such as sand, kaolinites or granulated inert material. Also suitable active ingredients in the usual manner for the production of fertilizer granules, if desired in Mixture with fertilizers, be granulated.

Spritzη spray powders, the active ingredient concentration is, for. about 10 to 90% by weight, the remainder to 100% by weight consists of conventional

Formulation components. For emulsifiable concentrates, the concentration of active ingredient may be about 5 to 80% by weight. Dusty formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 2 to 20 wt .-%. For granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which Granuiierhilfsmittel, fillers, etc. are used. In addition, the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, Emulsifying, penetration, solvents, fillers or carriers. For use, the concentrates present in commercially available form are optionally diluted in the usual 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 not before use

more diluted with other inert substances.

With the external conditions such as temperature, humidity, u.a. the required application rate varies. She can be inside

continue to fluctuate borders, z. Between 0.005 and 10.0 kg / ha or more of anhydrous substance, but is preferably between 0.01 and 5 kg / ha.

Also mixtures or mixed formulations with other agents, win z. As insecticides, acaricides, herbicides, Fertilizers, growth regulators or fungicides may be possible. embodiment

The invention is explained in more detail by the following examples

 formulation Examples

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

B. 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 inert material, 1 part by weight of lignosulfonic acid potassium and 1 part by weight of sodium oleoylmethyltaurate as wetting and dispersing agent and grinding in a pin mill.

C. A dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of active compound with 6 parts by weight of alkylphenol polyglycol ether (Triton χ 207), 3 parts by weight of isotridecanol polyglycol ether (8 AeO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, from about 255 ^° C. to above 377 ^° C) and ground in a ball mill to a fineness of less than 5 microns.

D. An emulsifiable concentrate is obtained from 15 parts by weight of active compound, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated Noi> ylphenol (10 AeO) as an emulsifier.

Chemical examples example 1 N- (2-methoxyethyl) -5- (2, e-dichloro-4-trifluoromethylphenoxy) -2-nitro-phenyl-acetamide

4.10 g (0.01 mol) of 5- (2,6-dichloro-4-trifluoromethylphenoxy) -2-nitro-phenylacetic acid are refluxed in 50 ml of thionyl chloride for 2 hours and after distilling off the excess thionyl chloride in vacuo with a mixture of 0 , 75g (0.01 mol) of 2-methoxyethylamine and 1.01 g (0.01 mol) of triethylamine in 60 ml of tetrahydrofuran (THF). After stirring for one hour at room temperature, it is added to ice-water, extracted with diethyl ether, the ether extract with saturated NaHCO ₃ solution (20 ml) and washed with water (50 ml), dried over Na ₂ SO ₄ and concentrated in vacuo. There remain 4.12 g (88% of theory) of N- (2-methoxy-ethyl) -5- (2,6-dichloro-4-trifluoromethyl-phenoxy) -2-nitro-phenylacetamide as a white solid of mp. 120 ^c C to 122 ⁰ C back.

Example 2

1-Ethoxycarbonyl-ethyl-5- (2,6-dichloro-4-trifluoromethyl-phenoxy) -2-nitro-phenylacetate 4.10g (0.01 mol) of 5- (2,6-dichloro-4-trifluoromethylphenoxy) -2 -nitro-phenylacetic acid are dissolved in BOmI dioxane and admixed with 1.62 g (0.01 mol) of carbonyldiimidazole. After completion of the gas evolution is stirred for a further V2 hours at room temperature and treated with 1.18 g (0.01 mol) of ethyl lactate, stirred for 6 hours at room temperature, added to ice water and extracted with diethyl ether. Wash or ether phase with saturated NaHCO ₃ solution and water, dry over

Na ₂ SO ₄ and concentration in vacuo gives 4.29 g (84%) of 1-ethoxycarbonylethyl-5- (2,6-dichloro-4-trifluoromethylphenoxy) -2-nitro-

phenylacetate as an amber wax.

The following compounds of the formula I can be prepared analogously, see Table 1. Table 1

X R ¹ CH-C-Y Y Mp Γ ⁰ Cl Cl H I ₁ Il R ¹ O NHCH ₃ 194/96 Verb.-Nr. Cl H NH (CH ₂ ) ₃ CH ₃ 141/44 3 Cl H NHCH (CH ₃ ) COOC ₂ H ₅ 113/15 4 Cl H NHCH ₂ -C ₆ H ₅ 183/85 5 Cl H NH-C ₆ H ₄ -2 Cl 6 Cl Π NHCH ₂ CH ₂ CONH ₂ 7 Cl H N (CH ₃ ) CH ₂ CH ₂ Si (CH ₃ J ₃ 8th CH ₃ 9

HN (CH ₃ J- (CH ₂ J ₂ -Si-CH ₃

CH ₃

11 Cl H N (CH ₃ ) OCH ₃ 39/41 12 Cl H OCK ₂ COOCH ₃ wax 13 Cl H OCH ₂ COOCH (CH ₃ J ₂ wax 14 Cl H OCH ₂ COOCH ₂ Ch ₂ CI wax 15 Cl H

Cl

OCH ₂ COOCH ₂ -C ₆ H ₅

17 Cl H OCH (CH ₃ ) COOH 18 Cl H O-CHCOOH I CH ₂ COOH 19 Cl H 0-CH (CH ₃ ) COONa 20 Cl H OCH (CH ₃ ) COOK 21 Cl H 0 (CH ₂ J ₂ COOH 22 Cl H OCH (CH ₃ ) CONHCH (CH ₃ ) ₂ 23 Cl H O (CH ₂ ) ₂ CONH ₂ 24 Cl H OCH (C ₂ H ₅ ) COOC ₂ H ₅

Table 1 (continued) X rl Y Fp [ ⁰ Cl Verb.-Nr. Cl H OCH (C ₂ H ₅ ) COOH 25 Cl H OCH (CH ₃ ) CONHN-C ₆ H ₁₃ 26 Cl H 0 (CH ₂ J ₂ CONHCH ₂ - ^ j) 27 Cl H OCH (CH ₃ J CONH-CH ₂ -C ₆ H ₄ -2 Cl 28 Cl H OCH (CH ₃ J CH ₂ CONH-C ₆ H ₅ 29 Cl H OCH (CH ₃ JCOO-C ₆ H ₄ -4-Cl 30 Cl H OCH (CH ₃ J CONH-C ₆ H ₃ -2,4-Cl ₂ 31 Cl II OCH (CH ₃ J CONH-C ₆ H ₄ -4 -OCH ₃ 32 Cl H 0 (CH ₂ ) ₂ COOH (CH ₂ J ₂ CN 33 Cl H SCH ₂ COOC ₂ H ₅ wax 34 Cl H SCH (CH ₃ ) COOCH ₃ wax 35 Cl H S (CH ₂ J ₂ COOC ₂ H ₅ 36 Cl H SCH ₂ COOCh ₂ - ^ J) 37 Cl H SCH (CH ₃ J CONHCH ₂ - C ₆ H ₅ 38 Cl CH ₃ NHCH (CH ₃ J ₂ 39 Cl CH ₃ NH (CH ₂ J ₂ OCH ₃ 40 Cl CH ₃ OCH (CH ₃ ) COOCa / 2 41 Cl CH ₃ OCH (CH ₃ J CONH (CH ₂ ) ₂ CH ₃ 42 Cl CH ₃ SCH (CH ₃ J COOCH ₂ Si (CH ₃ ) ₃ 43 Cl CH ₃ S (CH ₂ ) ₂ COOCH ₂ CHCH 44 Cl OCH ₃ OCH ₂ COOCH ₂ Ch ₂ Cl π 45 Cl OCH ₃ Il OCH ₂ CSCH ₃ 46 Cl OCH ₃ 0 Il SCH (CH ₃ ) CSC ₂ H ₅ 47 F H NHCH ₂ CH ₂ CN 48 F H NHCH ₂ CH = CH ₂ 49 F H NHCH (CH ₃ ) CON (CH ₃ J ₂ 50 F H NHCOOC ₂ H ₅ 51 F H NH-C ₆ H ₄ -4-OCH ₃ 52 F H NHCH ₂ -C ₆ H ₄ -4 -CH ₃ 53 F H OCH ₂ COOC ₂ H ₅ wax 54 F H OCH (CH ₃ ) COOCH ₃ wax 55 F H OCH (CH ₃ ) COOC ₂ H ₅ wax 56 F H OCH ₂ COOCH ₂ -C ₆ H ₅ 57

(Continuation) • F rl Y -8- 283 318 Fp r ° ci Table 1 No. X F H OCH ₂ COOCH ₂ - ^ l) Verb. F F H OCH ₂ COO (CH ₂ J ₂ -C ₆ H ₄ -4 Cl 58 F F H OCH-COOC ₂ H ₅ wax 59 F F CH ₂ -COOC ₂ H ₅ 60 F H OCHCOOC ₂ H ₅ F F C ₆ H ₅ 61 F H OCH (CH ₃ ) CONH (CH ₂ ) ₃ CH ₃ F H OCH (CH ₃ ) CONH (CH ₂ ) ₂ OCH ₃ 62 H OCH (CH ₃ ) CONH- / J 63 F H OCH ₂ CH ₂ COO-CyClOhBXyI 64 F H OCH (CH ₃ ) CONHCH ₂ COOc ₂ H ₅ 65 F H OCH (CH ₃ ) CONHCH ₂ - C ₆ H ₅ 66 F CH ₃ NHCH ₂ - / j] 67 F CH ₃ OCH (CH ₃ ) COOCH ₃ 68 F CH ₃ OC (CH ₃ J ₂ COOC ₂ H ₅ 69 F COOC ₂ H ₅ 70 F CH ₃ O (CH ₂ ) ₂ CONHCHCH ₃ F C ₂ H ₅ OCH (CH ₃ ) CON (C ₂ H ₅ J ₂ 71 Cl C ₂ H ₅ OCH ₂ COOC ₂ H ₅ 72 Cl C ₂ H ₅ NH (CH ₂ J ₃ SCH ₃ 73 CH ₂ Cl NH (CH ₂ J ₂ N (CH ₃ J ₂ 74 Cl CCl ₃ OCH ₂ COOCH ₃ 75 Cl OCH ₃ NH ₂ 76 Cl OCH ₃ OCH ₂ COOCH ₃ 77 F OCH ₃ OCH ₂ CONHC ₂ H ₅ 78 F H S (CH ₂ J ₂ COOCH ₃ wax 79 Cl H -Ol «| ~ COOC ₂ H ₅ Wax; 80 Cl CH ₃ [α] 25 = _ι _6/1 ο 81 H NH ₂ 184/86 H OC (CH ₃ J ₂ COOCH ₃ wax 82 H 0 (CH ₂ ) COOC ₂ H ₅ wax 83 H NH (CH ₂ J ₂ OCH ₃ 134/36 84 H SCH ₂ COOC ₂ H ₅ wax 85 H OCH (CH ₃ ) CON (C ₂ H ₅ J ₂ wax 86 H OCH (C ₆ H ₅ ) COOC ₂ H ₅ 14 _5/47 87 88

Table 1 (continued) Part no. X

Mp [ ⁰ Cl

Cl Cl

Cl

Cl Cl Cl Cl

H H

H H H H

OCH (CH ₃ ) CONHCH ₂ C ₆ H ₅

CH ₃ OeI-COOCH ₃

CH ₃

OCH (CH ₃ ) CONH ₂ OCH (C ₂ H ₅ ) CONHCH ₂ C ₆ H ₅ OCH (CH ₃ ) CH ₂ COOc ₂ H ₅ OCH (CH ₃ ) COOCH (CH ₃ ) ₂

129/31 wax; [α] 25 = _ΐ8,95 <wax; [α] 25 = _{+ 18/0} °

78/80 129/31 wax wax

Biological examples

The damage to the weed plants or the crop plant compatibility was scored according to a key in which the

Effectiveness is expressed by values of 0-5. Where:

0 = no effect or damage

1 = 0-20% effect or damage

2 = 20-40% effect or damage

3 = 40-60% effect or damage

4 = 60-80% effect or damage

5 = 80-100% effect or damage

1. weed effect in the preliminary run

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were placed in sandy pots in plastic pots (diameter: 9 cm) and covered with soil. The compounds according to the invention formulated in the form of wettable powders or emulsion concentrates were then applied to the surface as aqueous suspensions or emulsions with a water application rate of 600-800 l / ha in different doses. 1er cover soil applied.

After treatment, the pots were placed in the greenhouse and under good growth conditions for the weeds

maintained (temperature: 23 plus / minus 2 degrees Celsius, relative humidity: 60-80 ⁰ C).

The visual assessment of the plant or the impact damage occurred after emergence of the test plants after a test period of 3-4 weeks compared to untreated controls. As shown by the scores in Table 1, the compounds of the present invention have good herbicidal pre-emergence activity against a broad spectrum of grass weeds and

Weeds on.

2. Weed effect postemergence

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in sandy loam soil in plastic pots (diameter = 9 cm), covered with soil and grown in the greenhouse under good growth conditions. Three weeks

after sowing, the test plants were treated at the trefoil stage.

The compounds according to the invention formulated as wettable powders or emulsion concentrates were sprayed onto the green parts of the plant in various dosages with a water application rate of 600-800 l / ha unnci after about 3-4 weeks life of the test plants in the greenhouse under optimum growth conditions (temperature.

23plus / minus 2 degrees Celsius, relative humidity 60-80%) the effect of the preparations optically compared to untreated

Controls scored.

The compositions according to the invention also have a good herbicidal activity against the broad spectrum postemergence

economically important grass weeds and weeds (Table 2).

3. crop compatibility

In further experiments in the greenhouse, seeds of a greater number of crops and weeds were placed in sandy loam soil and covered with soil.

One part of the pots was immediately treated as described under 1, the rest being set up in the greenhouse until the plants had developed two to three true leaves and then sprayed with the substances according to the invention in different dosages as described under 2.

Four to five weeks after application and service life in the greenhouse it was found by optical assessment that the compounds according to the invention have two-leaved cultures, e.g. Soy, cotton, oilseed rape, sugar beets and potatoes pre-emergence and post-emergence even with high doses of active ingredient undamaged. In addition, some substances also protected Gramineae crops such. As barley, wheat, rye, sorghum millet, corn or rice. The compounds according to the invention thus have a high selectivity when used for controlling unwanted plant growth in agricultural crops.

Table 2: Pre-run effect Example no. Dose kg a.i./ha herbicidal action SIA CRS STM LGM

1 2.5 2 2.5 3 2.5 4 2.5 5 1.25 6 1.25 12 2.5 13 1.25 34 1.25 56 1.25 80 1.25 81 1.25 82 1.25 83 1.25 84 1.25 85 1.25 86 1.25 87 1.25 88 1.25 89 1.25 90 1.25 91 1.25 92 1.25 93 1.25 Abbreviations: STA = Sinapis alba CRS = Chrysanthomum segetum STM = Stellaria media LOM = Lolium multiflorum ECG = Echinochloacrus galli

Example 2: Post-emergence effect Example no. Dose kg ai / ha

5 5 5 5 2 4 2 4 5 5 5 5 5 5 5 2 5 5 5 5 5 5 5 4 5 5 5 5 5 3 5 5 5 5 4 3 2 2 5 5 3 4 4 5 5 2 4 5

5 5 5 5 5 4 5 5 5 5 5 5 5

5 5 5 5 3 2 5 5 5 5 5

5 5 3 4 2 4 3 3 5 4 5 5 5 2 2 4 5 5 5 3 5 3 3 4 5 2 2 3 2 5 5 5 5 2 2 1 1 4 2 3 1 2 2 2 1 2 0

herbicidal action SIA CRS STM LOM

ECG

1 2 3 4

2.5 2.5 2.5 2.5

5 5 5 4

5 5 4 4

5 4 2 2

-11- 283 318 Continuation Table 2 Example no. Dose herbicidal action

kg ai / ha SIA CRS S TM LOM ECG

5 1.25 5 5 5 5 5 6 1.25 3 4 5 4 3 12 2.5 5 5 5 2 2 13 1.25 5 5 5 4 4 34 1.25 5 5 5 3 5 56 1.25 5 5 5 5 5 80 1.25 5 5 5 3 5 81 1.25 5 5 5 3 3 82 1.25 3 4 4 2 4 83 1.25 5 5 5 2 3 84 1.25 5 5 5 3 4 85 1.25 5 5 5 5 5 86 1.25 5 5 5 5 5 87 1.25 5 5 4 2 · 4 88 1.25 5 5 3 2 3 89 1.25 5 5 4 2 3 90 1.25 5 5 5 1 1 91 1.25 5 5 5 1 2 92 1.25 5 5 5 4 4 93 1.25 4 3 3 1 2 94 1.25 5 5 5 2 3

Claims (3)

1. A herbicidal composition, characterized in that it comprises an effective amount of a compound of the formula I ₁ CH-CY
I. Il
R ¹ O X halogen, Y a rest of the formulas W O or S, ZO, S or NR ¹ , η 1,2,3 or 4, R ¹ , R ⁴ independently of one another are hydrogen, (C ₁ -C ₄ ) AlKVl, (C ₁ -C ₄ ) alkoxy or halogen (C ₁ -C ₄ -alkyl), R ^2, R ³ are independently hydrogen, (C ₁ -C ₄₎ -alkyl which is mono- or polysubstituted by halogen and / or mono- or disubstituted by cyano, (Ci-C ₄₎ AI koxy, (C \ -C ₄ ) Alkylthio, di (C 1 -C ₄ ) alkylamino, carboxy, (C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, (C 1 -C 4 -alkylaminocarbonyl,
Diid-GOalkylaminocarbonyl, Tn (C ₁ -C ₄ -alkyl ₎ silyl, unsubstituted or (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy or halogen-substituted phenyl, furanyl or thienyl, (C ₂ -C ₆ ) Alkenyl, (C ₇ -C ₆ ) AlkInYl, (CH ₁ -C ₄ ) alkoxy-carbonyl, phenyl which may be substituted by (C ₁ -C ₄ ) alkyl, halogen, cyano or (C ₁ -C ₄ ) alkoxy, or (C ₁ -C ₄ ) AIkOXy and R ^{5 is} hydrogen, (C ₁ -C ₀ ) alkyl, which is mono- or polysubstituted by halogen and / or mono- to two times by nitro, cyano, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) AlkYuhJo, Tn (C ₁ -C ₄ alkyl ₎ silyl, unsubstituted or by (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) Alkenoxy or halogen-substituted phenyl, furanyl or thienyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₆ -C ₇ ) CyClOalkyl, phenyl which may be substituted by (C ₁ -C ₄ ) C ₄ ) Alkenyl, (C ₁ -C ₄ ) alkoxy, halogen or Cayno may be substituted, or in case Z = NR ^{1 is} a residue (C ₁ -C ₄ ) alkoxy or their salts or stereoisomers in combination with customary auxiliaries for crop protection formulations. 2. A herbicidal composition according to claim 1, characterized in that in the formula I. Y -W- (CR ² R ⁴ I _n -CZR ⁵ , W Ooder, ZO, S or NR ¹ η 1 or 2, R ^{1 is} H or CH ₃ , R ² HOdOr (C ₁ -C ₄ ) alkyl, R ^{4 is} H, (C ₁ -C ₄ ) alkyl, which may be substituted by halogen, (C ₁ -C ₄ ) alkoxy or benzyl means and
R ^{5 has} the meaning given in claim 1. 3. A process for the preparation of the compounds of formula I according to claim 1 or 2, their isomers and salts, characterized in that a) a compound of formula II (II) CH-CY
I. Il
R ¹ O by reaction with a nitrating agent, or b) for R ¹ = H, a compound of formula III