DD268686A5 - PROCESS FOR THE PREPARATION OF ALKYL-N-ARYL-TETRAHYDROPHTHALIMIDES - Google Patents

Abstract

The invention relates to a process for the preparation of alkyl-N-aryl-tetrahydrophthalimiden of the formula I, in which z. B. reacting a compound of formula II with a compound of formula III in the presence of water or an organic solvent. The compounds according to the invention have advantageous herbicidal properties.

Description

X ₁ Y oxygen,

R ₁ is oriented in position 4 and methyl,

R _{2 is} chlorine or bromine,

R _{3 is} (C ₁ -C ₄ ) alkyl, halo-Fe-Q-alkyl, (C ₃ -C ₄ ) alkenyl; (C ₃ -C ₄ ) alkynyl;

(C ₁ -C ₄₎ alkoxycarbonyl (C, -C ₄₎ alkyl; cyano (C ₁ -C ₄₎ alkyl; Bonzyl substituted up to two times by halogen, (C, -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or CF ₃

is or a residue of the formula

Z-R

or

η · 1 and

m = 1 or 2.

3. Use of compounds of the formula I according to claim 1 or 2 as herbicides.

4. Herbicidal agents, characterized in that they contain, in addition to customary formulation auxiliaries, a compound of formula 1 according to claim 1 or 2.

5. A method for controlling undesirable plants, characterized in that applying an effective amount of a compound of formula I of claim 1 or 2 on the crop areas or plants to be treated.

Field of application of the invention

The compounds prepared according to the invention are used as crop protection agents.

Characteristic of the known state of the art

Certain alkyl-N-aryl-tetrahydrophthalimides and their herbicidal activity are described in DE-A 3109035 (US Pat. No. 4,594,099) and JP-A 49,006,121.

Furthermore, the herbicidal activity of certain N-aryl-tetrahydrophthalimides is known which have no alkyl group in the phthalimide radical, s. EP-A 095192.

Object of the invention

The invention provides novel alkyl-N-aryl-tetrahydrophthalimides having selected substitutional species in the aryl moiety which, surprisingly, possess significantly higher herbicidal activities and at the same time exhibit excellent compatibility with crop plants.

The compounds of the invention forms! I have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous weeds. Also difficult to control perennial weeds, which expel from rhizomes, Wurzelstöckchen or other permanent organs, are well detected by the active ingredients. Examples of such harmful plants are various types of Avena, Lolium, Alopecurus, Phalaris, EcSnochloa, Digitaria, Setaria, Cyperus, Agropyron, Cynodon, Imperata, Sorghum, Galium, Viola, Veronica, Lamium. Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon, Sida, Convolvulus, Cirsium, Rumex, Artemisia, Sagittaria, Auria, Eleocrmris and Scirpus. It does not matter whether the substances are applied in pre-sowing, pre-emergence or post-emergence ancestors.

Explanation of the essence of the invention

The invention has for its object to provide novel alkyl-N-aryl-tetrahydrophthalimide with herbicidal activity.

The present invention relates to the tetrahydrophthalimides of the formula I

X 3

wherein X, Y, ZR ₁

independently of one another O or S, (C, -C ₄ ) alkyl,

Fluorine, chlorine, bromine or NO ₂

<C, -C ₄ ) alkyl, halogeno (C, -C ₄ ) alkyl, (CHMcycloalkyl, (C ₃ -C ₄ ) alkenyl, (C ₃ -C ₄ ) alkyl, cyano (C, C ₄ ) alkyl, (C, -C,) alkoxy- (C, -C ₄₎ alkyl, (C, -C ₄₎ alkylthio (C, -C ₄₎ alkyl, (C ₁ -C ₄₎ alkoxycarbonyl (C, -C ₄₎ alkyl, wherein the alkoxy part up to

May be substituted 3-fold by halogen,

(C, -C ₄₎ alkylthiocarbonyl (C, -C ₄₎ alkyl, (C, -C ₄₎ alkoxythiocarbonyl (C, -C ₄₎ alkyl, (C, -C ₄₎ alkoxy (C ₁ -C ₄₎ alkoxycarbonyl (C, -C ₄₎ alkyl, (C, -r,) alkoxycarbonyl (C, -C ₄₎ alkoxycarbonyl (C, -C ₄₎ alkyl, phenyl or phenyl (C _t -C ₄₎ alkyl, wherein the phenyl ring of the both radicals up to 3-fold by halogen, (C, -C ₄ ) alkyl, (Ci-C ₄ ) alkoxy, (Ci-C ₄ ) alkoxycarbonyl, CF ₃ . NO ₂ or CN may be substituted, or a residue of the formulas

Z-R

Z-R6

or

R _{4 is} hydrogen or (Ci-C ₄ ) alkyl,

Rs, Re (C ₁ -C ₄ ) AlkVl ° of the two radicals together an ethylene or propylene chain,

R ₇ , R ₈ are each independently hydrogen, (Ci-C ₄ ) alkyl, phenyl or benzyl, both in the phenyl toil by up to two times by (C | -C ₄ ) alkyl, halogen, (Ci-C ₄ ) alkoxy, CF ₃ , NO ₂ or CN may be substituted; or R ₇ and R ₈ , together with the N atom linking them, form a 5- or 6-membered saturated heterocycle which, as a ring member, may also contain an oxygen atom or a group> NR ⁴ and which may be substituted by (C) -C ₄ up to twice Alkyl may be substituted on the CH ₂ ring members,

η 1 or 2 and

m 1,2 or 3

mean.

Alkoxy, alkyl, alkenyl or alkynyl can be straight-chain or branched in the above definitions.

Particularly suitable heterocycles for the radical -NR7R8 are pyrrolidine, piperidine, piperazine, morpholine, or 2,6-dimethylmorpholine. Halogen (C 1 -C ₄ ) alkyl may contain up to six halogen, in particular fluorine or chlorine atoms, and is, for example, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 1,1,2 Trifluoro-2-chloro-ethoxy or 1,1,2,3,3,3-hexafluoropropoxy.

Preferred compounds of the formula I are those in which X, Y is oxygen, R ₁ is oriented in position 4 and methyl, R _{2 is} chlorine or bromine, R _{3 is} (C, -C) alkyl, halogen (C, -C ') - alkyl, (C ^ JAIkenyl; _(Cj-C4) alkynyl, (C ^ C ^ CJAIkoxycarbonyKC-alkyl; cyano (C, -C ₄₎ alkyl; benzyl which up to two times by halogen, (C ₁ -C ₄₎ -alkyl, (C ₁ - C ₄₎ -alkoxy or CF a ₃ is substituted or a radical of the formula!

/ R ₄ A ZR ₆ / RA

- \ pH / _m -CH, - ^ CH / mCN

, ^ / mCN or

ZR ₅ 0 ^X R ₈

/ ^Ν = η

CH2-N

η = 1 and m = 1 or 2.

For R ₃ is of particular importance (C ₁ -C ₄₎ -alkyl, (Ci-C ₄₎ alkenyl, (C ₃ - C ₄₎ alkynyl, (C, -C ₄₎ alkoxycarbonyl (C, - dialkyl, CyanolCt-C Alkyl or benzyl, which may be up to ₂ times substituted by halogen or (Ct-C4) alkyl.

Another object of the invention are ancestors for the preparation of compounds of general formula I, characterized in that

a) eiii? Compound of the formula (II) with a compound of the formula (III)

(III)

in the presence of water or an organic solvent, or b) a compound of the formula (IV)

^N V ~ Y ~ ^R 2 ^R 3 -Hal (V)

ZH

with a compound of formula (V) in the presence of a base and an organic solvent. As organic solvents in process a), for example, aromatic solvents such as toluene or xylene, glacial acetic acid or dimethylformamide can be used. The reaction temperature generally varies between 6O ⁰ C and 14O ⁰ C.

The reaction can also by acidic catalysts such. As sulfuric acid or p-toluenesulfonic acid, or by basic catalysts such. As pyridine or triethylamine, accelerated grazing.

In process variant b), the solvents used are, for example, aromatic solvents, such as toluene, and also acetone, acetonitrile, dimethyl sulfoxide or dimethylformamide. As bases find inorgani; Before bases, for example, alkali metal hydroxides or carbonates such as NaOH, K ₂ CO ₃ or organic bases such as Trialkyl.imine, pyridine and similar use.

Reaction temperatures will vary 'm generally between 4O ⁰ C and 12O ⁰ C.

The tetrahydrophthalic anhydrides of the general formula II are z.T. known, s. J. Org. Chem. 12, 947) 713; J. Am. Chem. Soc. 72 (1950) 3732 or can be prepared according to the methods described therein.

The compounds of the formula IV are prepared by reacting compounds of the formula II with compounds of the formula VI F

/ "^ V \ TJ

receive.

Di6 reaction takes place analogously to the procedure described for a).

Compounds of the formulas III and VI are prepared by synthesis methods familiar to the person skilled in the art.

If the compounds according to the invention are applied to the surface of the earth before germination, then either the emergence of the weed seedlings is completely prevented, or the weeds grow up to the cotyledon stage, but then cease their growth and finally die within three to four weeks completely off.

Upon application of the active ingredients to the green parts of the plants postemergence also occurs very quickly after treatment, a drastic growth stop, and the weed plants remain in the growth stage available at the time of application or die after a certain time more or less quickly, so that in this way a harmful to the crop weed competition can be eliminated very early and sustainable by the use of the novel compounds of the invention.

Although the compounds of the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops such as e.g. As wheat, barley, rye, rice, corn, sugar beet, cotton and soybean only insignificant or not at all gescnädigt. For these reasons, the present compounds are very well suited for the active control of undesired plant growth in agricultural crops.

In addition, the compounds according to the invention have growth-regulatory properties in crop plants.

They regulate the plant's metabolism and can thus be used to facilitate harvesting, such as 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 storage can be reduced or completely prevented.

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 alkyl phenols, polyoxyethylated fatty alcohols, alkyl or alkyl phenyl sulfonates and dispersants, e.g. lignosulfonic acid sodium, 2,2'-dinaphthyimethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or oleoylmethyltaurine acid. The preparation is carried out in a conventional manner, for. B. by grinding and mixing of the components.

Emulsifiable concentrates may, for. B. by dissolving the active ingredient in an inert organic Lösungsmit. ^p i, z. As 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 proportion of solvent can also be completely or partially eliminated.

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 substance with finely divided, solid substances z. Talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.

Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying active substance concentrations by means of binders, for. As 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 granulated in the manner customary for the production 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 concentration of active ingredient may be about 5 to 80% by weight.

Dust-form formulations usually contain 5 to 20% by weight of active ingredient, sprayable solutions 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 active substance formulations mentioned optionally contain the usual adhesion, wetting, dispersing, emulsifying, penetrating, solvent, filling or carrier substances.

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

in wettable powders, env gable concentrates, dispersions and sometimes also in microgranules by means of water.

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

With the external conditions such as temperature, humidity and the like. the required application rate varies. It can vary within wide limits, eg. For example, from 0.005 to 10.0 kg / ha or more of the active ingredient, but is preferably between 0.01 and 5 kg / ha.

Also mixtures or mixed formulations with other active ingredients, such as. As insecticides, acaricides, herbicides, fertilizers, growth regulators or fungicides may be possible. The invention is further illustrated by the following examples.

Av

hormulierungsbeispiele

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

B. A wettable powder readily dispensable in water is obtained by mixing 25 parts by weight of active ingredient, 64 parts by weight of kaolin-containing quartz, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of sodium oleoylmethyltaurine as wetting and disperging agents Pin mill grinds.

C. An ίη * Λ, ".: ·· q» · <-; -! ♦ disp:, ismares dispersion concentrate is obtained by adding 20 parts by weight of active substance

6 parts by weight of Aikylphenolpolyglykolether (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, about 255 to about 377 ⁰ C) mixed 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 ingredient, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol (10AdO) dls emulsifier.

Chemical examples example 1 N- (4-chloro-2-fluoro-5-methoxy-phenyl) -4-methyl-3,4,5,6-tetrahydrophthalimide

8.3 g (0.05 mol) of 4-methyl-3,4,5,6-tetrahydrophthalic anhydride and 8.8 g (0.05 mol) of 4-chloro-2-fluoro-5-methoxy-aniline are dissolved

in 120 ml of glacial acetic acid and stirred at 100 ⁰ C.

It is poured on ^r -nließend to 300ml of water, filtered off the precipitate and crystallized from ethanol.

This gives 11.7 g (72% of theory) of N- (4-chloro-2-fluoro-5-methoxyphenyl) -4-methyl-3,4,5,6-tetrahydrophthalimide in the form of colorless

Crystals with mp 107--110 ⁰ C.

Example 2 N (4-chloro-2-fluoro-5-propargyloxy-phenyl) -4-methyl-3,4,5,6-tetrahydrophthalimide

3,3 g (0.05 mol) of 4-methyl-3,4,5,6-tetrb-hydrochlorophthalic anhydride and 9.1 g (0.05 mol) of 4-chloro-2-fluoro-5-hydroxy-aniline are dissolved in

100 ml of glacial acetic acid stirred at 100 ⁰ C for 3h.

It is poured onto 300 ml of water and filtered off the precipitate.

This is dissolved without further purification in 130ml DMF. 8.3 g (0.06 mol) of potassium carbonate and 6.0 g (0.05 mol) are added.

Propargyl bromide and stirred for 5h at 7O ⁰ C.

It is poured onto 400 ml of water and filtered off the precipitate. After recrystallization from ethanol, 14.3 g (82% of theory) of N- (4-chloro-2-fluoro-5-propargyloxy-phenyl) -4-methyl-3,4,5,6-tetrahydrophthalimide are obtained in the form light beige crystals

with mp 104-106 ° C.

Example 3 N- (4-chloro-2-fluoro-5-methoxycarbonylmethoxy-phenyl) -4-methyl-3,4,5,6-tetrahydrophthalimide

8.3 g (0.05 mol) of 4-methyl-3,4,5,6-tetrahydrophthalic anhydride and 11.7 g (0.05 mol) of 4-chloro-2-fluoro-5-

methoxycarbonylmethoxy-aniline are dissolved in 150 ml of xylene. After addition of 1 ml of triethylamine is added to the water

heated to the completed formation of water.

It is washed with 100 ml of 2N hydrochloric acid and then with 100 ml of water, the organic phase is dried over sodium sulfate and the solvent is removed by distillation under reduced pressure. After drying under high vacuum, 17.4 g (91% of theory) of N- (4-chloro-2-fluoro-5-methoxycarborylmethoxy-phenyl) -4-methyl-3,4,5,6-

tetrahydro-halo-imide in the form of a light brown syrup.

In an analogous manner, the compounds of Table 1 below can be obtained.

Table 1 R ₁ R ₁ R ₃ Z X Y Fp [ ⁰ C] example -CH ₃ Br -CHZ-C * CH 0 0 0 syrup A -CH ₃ -Cl -CH ₂ -CH-CH ₂ 0 0 0 syrup 5 -CH ₃ -Cl -CH ₂ ^ O) -Cl 0 0 0 107-109 6 -CH ₃ -Cl -CH-CO ₂ C ₂ H ₃ CH ₃ 0 0 0 syrup 7 -CH ₃ Br -CH ₂ -CN 0 0 0 8th -CH ₃ -Cl -CH ₂ -CN 0 0 0 9 -CH ₃ Br -CH ₂ -CH (OC ₂ He) ₂ '0 0 0 10

-CH ₃ -Br -CH ₂ -CH ^

-CH ₃

Br

13 -CH ₃ Br -CH (CH ₃ ) ₂ IA -CH ₃ -Cl -CH (CHa) ₂ 15 -CH ₃ Br - (ο) 16 -CH ₃ Br -CH-CO ₂ CzHb CH ₃ 17 -CH ₃ -Cl -CH ₂ -CO ₂ CH ₃ 18 -CH ₃ -Cl -CH-CO ₂ C ₂ H ₈ 6η ₃

0 0 0 0 0 0

0 0

0 0 0

0 0

syrup

Syrup syrup

Continuation Table 1 Example R ₁ R ₂

R ₃

Mp ⁰ Cl

19 -CH ₃ Br -CH ₃ S 0 0 syrup 20 -CH ₃ Br -CH ₂ -C = OH S 0 0 21 -CH ₃ -Cl -CH (CH ₃ ^ S 0 0 22 -CH ₃ -Cl -CH ₂ -COzCH, CHz-OCH ₃ S 0 0 23 -CH ₃ -Cl -CHz-COzCH-COzCzHe CH ₃ 0 0 0 24 -CH ₃ -Cl -CHz-COzCHzCF ₃ 0 0 0 25 -CH ₃ -Cl -CH-COzCHzCF ₃ CH ₃ 0 0 0 26 -CH ₃ -Cl -CF ₂ -CHF ₂ 0 0 0 27 -CH ₃ -Cl -CF ₂ -CHFCl 0 0 0 28 -CH ₃ -Cl -CF ₂ -CHF-CF ₃ S 0 0 29 -CH ₃ _C1 -CHF ₂ 0 0 0 30 -C ₂ H ₈ -Cl -CH ₃ 0 0 0 31 -CH ₇ Br -CH ₂ -C-CH 0 0 0 32 -CH ₃ NO ₁ -CH ₃ 0 0 0 33 -CH ₃ NO ₂ -CH ₂ -C =CH 0 0 0 34 -CH ₃ NO ₂ -CH ₂ -CO ₂ CH ₃ S 0 0 syrup 35 -CH ₃ NO ₂ -CH-CO ₂ C ₂ H ₈ CH ₃ S 0 0 36 -CH ₃ Br -CH ₂ -CH = CH ₂ 0 0 0 37 -CH ₃ Br -CH ₂ -QN ^ 0 0 0

ro

crt

oo

σ> oo

Continuation table example R ₁ R,

R ₃ ZX

Mp [° C]

33

-CM ₃ -Br

40 -CH ₃ -Br -CH ₂ -I

/ N = T

41 -CH ₃ -Cl-CH ₂ -NI

-CH ₃ -Cl-CH ₂ -N

0 0 0

0 0 0

0 0 0

SOO

syrup

43

-CH ₃ -Br -CH ₂ -C-NCI

0 0 0

syrup

I I K)

C. 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 = O- 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 pre-emergence

Seeds or rhizomes of monocotyledonous and dicotyledonous weed plants were placed in sandy loam soil in plastic pots (0 = 9 cm) and covered with Erdo. The compounds according to the invention formulated in the form of wettable powders or emulsion concentrates were then applied to the surface of the cover soil as aqueous suspensions or emulsions having a water application rate of 600 l / ha in different dosages.

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

Weed plants kept (temperature 23 plus / minus 1 "C, relative humidity 60-80%).

The optical assessment of the plants or emergence damage occurred after emergence of the test plants after a

Trial period of 3-4 weeks compared to untreated controls.

The rating values show that the compounds of the present invention exhibit good hot bake-on pre-emergence activity

possess broad Spfik'rum of weeds and weeds, s. Table 2.

Table 2 dose ECG = SIA CRS herbicidal action ECG LOM Example- (Kgn.i./ha) ioaetum LOM = 5 5 STM 5 5 No. 2.5 5 5 5 5 5 1 2.5 5 5 5 2 3 2 2.5 5 5 3 4 4 3 2.5 5 5 5 5 5 4 2.5 5 5 5 5 5 5 2.5 5 5 5 5 5 14 2.5 5 5 5 3 4 36 2.5 3 43 Echinochloa crus-galli Abbreviations: Lolium multiflorum SIA = Sinapisarvensis CRS = Chrysanthemum ι

STM = Stellaria media

2. weed effect postemergence

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

Sowing, the test plants were treated in the three-leaf stage.

The compounds according to the invention formulated as wettable powders or emulsion concentrates were sprayed onto the green plant parts in various dosages with a conversion rate of 600 l / ha and after about 3-4 weeks life of the test plants in the greenhouse under optimum growth conditions (temperature 23 plus / minus 1 ⁰ C, relative humidity 60-80%) the effectiveness of the preparations optically compared to untreated controls

scoring.

The compounds according to the invention have good post-emergence herbicidal activity against a broad spectrum

economically weeds weeds and weeds, s. Table 3.

Table 3 Dose (kga.i./ha) SIA CRS herbicidal activity STM ECG LOM Example no. 2.5 5 5 5 5 5 1 2.5 5 5 5 5 4 2 2.5 5 5 5 3 2 3 2.5 5 5 5 5 5 4 2.5 5 5 5 4 5 5 2.5 5 5 5 5 5 14 2.5 5 5 5 4 2 36 2.5 5 5 5 2 3 43 Abbreviations: SIA = Sinapisiirvensis ECG CRS = Chrysanthemum segetum LOM STM = Stellaria media = Echinochloa crus-galli = Lolium multiflorum

3. crop compatibility

In further experiments in the greenhouse, seeds of a larger number of crops were grown in sandy loam soil

designed and covered with earth.

Part of the pots were treated immediately as described under 1.; the rest were placed in the greenhouse until the plants had developed two to three true leaves and then with the substances according to the invention in different

Dosages as described under 2. sprayed.

Four to five weeks after the application and life in the greenhouse mittols optical Bonitur was found that the orfindungsgemäßin compounds dicotyledonous crops such. As soybean, cotton, oilseed rape, sugar beets and potatoes in pre- and post-emergence even at high doses of active ingredient Iingoschridigt left. Einigo substances were gentle

in addition, graminaceous crops such as e.g. Barley, sorghum, corn, wheat or rice. The compounds of formula I thus have a high Selektivi'.ät hei application for controlling unwanted plant growth in agricultural

important cultures.

Claims (2)

claims: (Cj-CeJCycioalkyl, (C ₃ -C ₄₎ AI keny !, (C ₃ -C ₄₎ AIkInYl, cyano (C ₁ -C ₄₎ alkyl, (C ₁ -C ₄₎ alkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkylthio (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) Al '<oxycarbonyl (C ₁ -C ₄ ) alkyl, wherein the alkoxy moiety Hs to Stach by halogen (C ₁ -C ₄ ) alkylthiocarbonyl (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxythiocarbonyl (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy (C ₁ -) C ₄ ) alkoxycarbonyl (C ₁ -C ₄ ) alkyl _/ (C <-C ₄ ) alkoxycarbonyl (C ₁ -C ₄ ) alkoxycarbonyl- (C ₁ -C ₄ ) -alkyl, phenyl or phenyl (C ₁ -C ₄ ) -alkyl, where the phenyl ring of the two radicals is up to 3-fold by halogen, (C _r C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C 12 alkoxycarbonyl, CF ₃ , NO ₂ or CN may be substituted, or a residue of the formulas or -GH-N ² N =. H R _{4 is} hydrogen or (C ₁ -C ₄ ) alkyl, R5, R6 (C ₁ -C ₄ ) AlkYl or both radicals together an ethylp. Or propylene chain, R ₇ , R _{8 are} independently hydrogen, (C ₁ -C ₄ ) AlkYl, phenyl or benzyl, both in im the phenyl moiety may be up to disubstituted by (C ₁ -C ₄₎ -alkyl, halogen, (C, -C ₄₎ alkoxy, CF _3, NO ₂ or CN; or R ₇ and R ₈ form, together with the N atom linking them, a 5- or 6-membered saturated heterocycle which as ring member can also contain an oxygen atom or a group NR ⁴ and which can be up to twice by (C ₁ -C ₄ ) alkyl may be substituted on the CH ₂ ring members, η 1 or 2 and m 1,2 or 3 mean, characterized in that one a) a compound of formula II with a compound of formula III Z-R (II) (III) in the presence of water or an organic solvent, or b) a compound of formula IV R ₃ -HaI with a compound of formula (V) in the presence of a base and an organic solvent. 2. The method according to claim 1, characterized in that compounds of formula 1 are prepared, wherein