WO1996038413A1

WO1996038413A1 - Herbicidal n-(1-methylethyl)-4-hetero substituted-3-substituted-pyrrolin-2-one derivatives

Info

Publication number: WO1996038413A1
Application number: PCT/EP1996/002280
Authority: WO
Inventors: Peter Wegner; Alfred Angermann; Thomas Wegmann; Jens Geisler; Jürgen Bohner; Richard Rees
Original assignee: Hoechst Schering Agrevo Gmbh
Priority date: 1995-05-30
Filing date: 1996-05-29
Publication date: 1996-12-05
Also published as: IL118268A0; ZA964443B; AU6002096A; DE19520816A1

Abstract

There are described new 4-hetero substituted pyrrolinone derivatives of general formula (I), in which R?1, R2, R3¿, A and E have the meanings given in the description, their preparation and their use as herbicides.

Description

HERBICIDAL N-(1-METHYLETHYL)-4-HETERO SUBSTITUTED-3-SUBSTITUTED-PYRROLIN-2-ONE DERIVATIVES This invention relates to new substituted pyrrolinones, their preparation and their useas herbicides. It is already that certain 3-phenylpyrrolin-2-ones (EP 0 372 586 and

EP 0 557 691) possess herbicidal activity. However the herbicidal activity of these compounds in not high enough or selectivityproblems can occur in important crops. The object of the present invention is to make new compounds that do not have these disadvantages and have improved biological properties over the known compounds. The object of the invention is solved by new 4-hetero substituted pyrrolinone derivatives of general formula I

in which

R¹ is C₁ -C₆-alkyl, halo-C₁ -C₆-alkyl, C₁ -C₆-alkoxy-C₁-C₆-alkyl or C₃-C₆-cycloalkyl, or phenyl, optionally substituted by the group X_m,

A is the group OR⁴, SR⁴, SOR⁴, SO₂R⁴ or NR⁵R⁶,

R² is hydrogen, C₁ -C₆-alkyl, C₁ -C₆-alkoxy, halogen, hydroxy, amino,

C₁ -C₆-alkylamino or C ₁-C₆-dialkylamino,

R³ is hydrogen, C₁ -C₆-alkyi or halogen,

R⁴ is hydrogen, C₁ -C₆-alkyl, halo-C ₁-C₆-alkyl. C₁ -C₆-alkoxy-C₁-C₆-alkyl,

C₂-C₆-alkenyl, halo-C₂-C₆ -alkeny!, C₂-C₆-alkinyl or C₃-C₆-cydoalkyl, or phenyl or benzyl, both of which are optionally substituted by the group X_m, or R⁴ is the group COR⁷, R⁵ is hydrogen, C₁ -C₆-alkyl, halo- C₁ -C₆-alkyl, C₁ -C₆-alkoxy-C ₁-C₆-alkyl,

C ₁-C₆-alkoxy, C₂-C₆-alkenyl, halo-C₂-C₆-alkeπyl, C₂-C₆-alkinyl,

C₃-C₆-cycloalkyl or hydroxy, or phenyl or benzyl, both of which are optionally substituted by the group X_m, or R⁵ is the group COR⁷,

R⁶ is hydrogen, C ₁-C₆-alkyl. halo-C₁ -C₆-alkyl, C ₁-C₆-alkoxy-C ₁-C₆-alkyl,

C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₆-cycloalkyl, or phenyl or benzyl, both of which are optionally substituted by the group X_m, or R⁶ is the group COR⁷,

R⁵ and R⁶ together with the nitrogen to which they are attached form a pyrrolidino, piperidino or morpholino group,

R⁷ is hydrogen, C ₁-C₆-alkyl, halo-C ₁-C₆-alkyl, C₃-C₆-cycloalkyl or phenyl, optionally substituted by the group X_m,

X is hydrogen, hydroxy, C ₁-C₆-alkyl, halo-C₁ -C₆-alkyl, C₁ -C₆-alkoxy-C₁ -C₆-alkyl, C ₁-C₆-alkoxy, mercapto, C ₁-C₆-alkylthio, C₁ -C₆-alkylsulfonyl, C ₁-C₆-alkyl- sulfinyl, amino, C₁ -C₆-alkylamino, C ₁-C₆-dialkylamino, halogen, cyano,

C₁ -C₆-alkoxycarbonyl, aminocarbonyl, C ₁-C₆-alkylaminocarbonyl,

C₁ -C₆-dialkylaminocarbonyl or nitro,

m is 1, 2 or 3, whereby when m is 2 or 3 the substituent X can be the same or different, E is the group -CO-R⁸ , the group

or one of the substituents selected from the group E-1 to E-6, each of which may be optionally substituted by the group X_m,

^

D is oxygen, sulfur, NH or N-C ₁-C₆-aikyl,

R⁸ is hydrogen, hydroxy, C ₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkinyl or phenyl or benzyl, both of which are optionally substituted by the group X_m, or R⁸ is the group OR⁹, the group OM or the group NR¹⁰R^{1 1}

R⁹ is hydrogen, C₁-C₆-alky!, benzyl, phenyl or phenyl optionally substituted by

C₁ -C₅-alkyl, C₁ -C₆-alkoxy, halogen or nitro,

R¹⁰ is hydrogen, hydroxy, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, or

C ₁-C₆-alkoxy, or phenyl or benzyl both of which are optionally substituted by the group X_m,

R^{1 1} is hydrogen, hydroxy, C ₁-C₅-alkyl, C₂-C₅-alkenyl, C₂-C₆-alkinyl, or

C₁ -C₆-alkoxy, or phenyl or benzyl both of which are optionally substituted by the group X_m,

R¹⁰ and R^{1 1} together with the nitrogen to which they are attached form a pyrrolidino, piperidino or morpholino group,

M is a cation selected from the group of lithium, sodium, potassium, one equivalent of from the group of zinc, manganese, calcium, barium or an ammonium ion possess better herbicide properties than the known compounds of related structure.

Preferred compounds are 4-hetero substituted pyrrolinone derivatives of

general formula I, in which

R¹ is phenyl, optionally substituted by the group X_m,

A is the group OR⁴, SO₂R⁴ or NR⁵R⁶,

R² is hydrogen,

R³ is hydrogen,

R⁴ is hydrogen, C₁ -C₆-alkyl, haio-C ₁-C₆-alkyl, C₁ -C₆-alkoxy-C ₁-C₆-alkyl or the

group COR⁷,

R⁵ is hydrogen, C₁ -C₆-alkyl or phenyl, optionally substituted by the group X_m,

R⁶ is hydrogen or C ₁-C₆-alkyl,

R⁷ is C₁ -C₆-alkyl, X is halogen, C₁ -C₆-alkyl, C₁ -C₆-alkoxy, halo-C₁ -C₆-alkyl or cyano,

m is 1 or 2, whereby when m is 2 the substituent X can be the same or different,

E is the group -CO-R⁸ or one of the substituents E-1 or E-6, each of which may be optionally substituted by C₁ -C₆-alkyl or phenyl,

D is sulfur or N-C₁ -C₆-alkyl,

R⁸ is hydroxy, C₁ -C₆-alkyl or the group NR¹⁰R^{1 1}

R¹⁰ is hydrogen and

R¹¹ is phenyl, optionally substituted by the group X_m.

The term "halogen" means fluorine, chlorine, bromine and iodine.

It is to be understood that the term "alkyl", "alkenyl" and "alkynyl" includes branched as well as straight chained hydrocarbon groups.

The compounds of formula I can optionally exist various enantiomeric,

tautomeric or geometric forms. These are also within the scope of the invention.

The compounds of the invention can be prepared, in known manner for example by a process in which

A) when the group A in the compounds of the invention of general

formula I is hydroxy, a compound of general formula II,

in which R¹ , R², R³, R⁹ and E are as decried in general formula I, is subjected to an intramolecular cyclisation, or B) when A in the compounds of the invention of general formula I, is the group OR⁴, a compound containing a hydroxy group of general formula la,

C) when A in the compounds of the invention of general formula I, is group NR⁵R⁶, a compound containing a hydroxy group of general formula la, is reacted according to process A with an alkylating agent of the general formula,

HNR⁵R⁶, where R⁵ and R⁶ have the meanings given above.

The intramolecular cyclisation according to process A) is suitably carried out in the presence of a base or acid and optionally an inert solvent or diluent.

Suitable bases are for example sodium or potassium hydroxide, sodium methanolate or ethanolate, sodium hydride, sodium or potassium carbonate or potassium tert.-butylate. Suitable acids include hydrochloric acid, sulfuric acid, acetic acid or Lewis acids, such as for example aluminium chloride or zinc chloride. As solvent or diluent especially valuable are tetrahydrofuran, toluene and ethanol.

Process B) is suitably carried out in the presence of an inert solvent or diluent and an acid binding agent. Suitable solvent or diluents are for example acetonitrile, tetrahydrofuran, dimethylformamide or toluene. Examples of acid binding agents are sodium or potassium hydroxide, sodium methanolate or ethanolate, sodium hydride, sodium or potassium carbonate or potassium tert.- butylate. Process C) is suitably carried out in the presence of an inert solvent or diluent, such as aliphatic or aromatic hydrocarbons, that are optionally halogenated. Examples are toluene, xylene, chlorobenzene, naphtha, hexane or

cyclohexane. The reaction is preferably carry out under anhydrous conditions for example by adding dehydrating agents, such as sodium or potassium sulfate or a molecular sieve. Also valuable is the azeotropic distilling of water during the reaction.

All reactions are preferably carried out at atmospheric pressure, although

higher or lower pressures may be used.

They can also be carried out over a wide temperature range. In general a

temperature of between -20°C and the boiling point of the reaction mixture, preferably at 0°C to 180°C.

The presence of a catalyst can be an advantage. Suitable catalysts include potassium iodide and onium compounds, such as quaternary ammonium, phosphonium and arsonium and suifonium compounds. Also suitable are polyglycol ethers, especially cyclic ethers, such as 18-crown-6, and tertiary amines, such as for example tributylamine. Preferred compounds are quaternary ammonium compounds, such as for example benzyltriethylammonium chloride and tetrabutylammonium bromide.

The compounds of the invention prepared by these processes can be isolated from the reaction mixtures in conventional manner, for example by distillation of the solvent at normal or reduced pressure, by precipitation with water or by extraction. A higher level of purity can be achieved as a rule by column chromatography as well as by fractional distillation or crystallisation.

The compounds of the invention are, as a rule, colourless and odourless liquids or crystals that have limited solubility in water, aliphatic hydrocarbons such as petroleum ether, hexane, pentaπe and cyclohexane and highly soluble in

halogenated hydrocarbons, such as chloroform, methylene chloride and carbon tetrachloride, aromatic hydrocarbons, such as benzene, toluene and xylene, ethers, such as diethyl ether, tetrahydrofuran and dioxane, nitriies, such as acetonitrile, alcohols, such as methanol and ethanol, amides, such as

dimethylformamide, and sulfoxides, such as dimethyl sulfoxide, or organic

bases, such as for example pyridine.

The starting materials for process A of general formula II can be prepared according to known literature methods. The compounds of the invention show a good herbicidal activity against broad leaf weeds and grasses. A selective use of the compounds of the invention in various crops is possible for example in rape, beet, soya beans beans, cotton, rice, barley, wheat and other cereals. Individual active substances are particularly suitable as selective herbicides in beet, cotton, soya beans, maize and cereals. However the compounds can be used for control of weeds in permanent crops, such as for example forestry, ornamental trees, fruit, vine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plantations. The compounds of the invention can used for example against the following plant species:

Dicotyledonous weeds of the species: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galiπsoga, Chenopodium, Brassica, Urtica, Senecio, Amaraπthus,

Portulaca, Xanthium, Convolvulus, Ipomoea, Polygoπum, Sesbania, Ambrosia,

Cirsium, Carduus, Soπchus, Solanum, Rorippa, Lamium, Veronica, Abutilon, Datura, Viola, Galeopsis, Papaver, Centaurea and Chrysanthemum.

Monocotyledonous weeds of the species: Avena, Alopecurus, Echinochloa, Setana, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron, Sagittaria, Monocharia, Fimbristylis, Eleocharis, Ischaemum and Apera.

The rates of use vary depending on the manner of pre- and postemergent use between 0.001 and 5 kg/ha.

The compounds of the invention can also be used as defoliants, desiccants and total herbicides.

The compounds of the invention can be used either alone or in admixture with one another or with other active agents. Optionally, other plant-protective agents or pesticides can be added, depending on the purpose for the treatment. When it is desired to broaden the spectrum of activity, other herbicides can also be added.

Herbicidally active mixing partners suitable in this connection include for example, the active agents listed in Weed Abstracts, vol. 40, No. 1 , 1991 , under the heading "Lists of common names and abbreviations employed for currently used herbicides and plant growth regulators in Weed Abstracts". An improvement in the intensity and speed of action can be obtained, for example, by addition of suitable adjuvants, such as organic solvents, wetting agents and oils.

Such additives may allow a decrease in the dose. The designated active ingredients or their mixtures can suitably be used, for example, as powders, dusts, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers and/or diluents and, optionally, binding, wetting, emulsifying and/or dispersing adjuvants. Suitable liquid carriers are, for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide,

dimethylformamide and other mineral-oil fractions and plant oils.

Suitable solid carriers include mineral earths, e.g. beπtonite, silica gel, talcum, kaolin, attapulgite, limestone, silicic acid and plant products, e.g. flours.

As surface-active agents there can be used for example calcium lignosulfonate, polyoxyethylenealkylphenyl ethers, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates, as well as substituted benzenesulfonic acids and their salts.

The percentage of the active ingredient(s) in the various preparations can vary within wide limits. For example, the compositions can contain about 10 to 90 percent by weight active ingredients, and about 90 to 10 percent by weight liquid or solid carriers, as well as, optionally up to 20 percent by weight of surfactant.

The agents can be applied in customary fashion, for example with water as the carrier in spray mixture volumes of approximately 100 to 1 ,000 l/ha. The agents can be applied using low-volume or ultra-low-volume techniques or in the form of so-called microgranules.

The preparation of these formulations can be carried out in known manner, for example by milling or mixing processes. Optionally, individual components can be mixed just before use for example by the so-called commonly used tank-mixing method. Formulations can be prepared, for example, from the following ingredients.

A) Wettable Powder

20 percent by weight active ingredient

35 percent by weight fuller's earth

8 percent by weight calcium lignosulfonate

2 percent by weight sodium salt of

N-methyl-N-oleyltaurine

25 percent by weight silicic acid

B) Paste

45 percent by weight active ingredient

5 percent by weight sodium aluminium silicate

15 percent by weight cetyl polyglycol ether with 8 mole ethylene oxide 2 percent by weight spindle oil

10 percent by weight polyethylene glycol

23 percent by weight water

C) Emulsifiable Concentrate

20 percent by weight active ingredient

75 percent by weight isophorone

5 percent by weight of a mixture of the sodium salt

of N-methyl-N-oleyltaurine and calcium

lignosulfonate

The following examples illustrate the preparation of compounds of the invention.

Example 1

1-[1-(3-Chlorophenylaminocarbonyl)-1-methylethyl]-4-hydroxy-3-phenylpyrrolin-2-one

1.1 g (35 mMol) Sodium hydride (80%) was added to 10 ml toluene To this, under reflux was added, dropwise, 11.9 g (30 mMol) methyl N-phenylacetyl-N-[1-(3-chloro- phenylaminocarbonyl)-1-methylethyl]aminoacetate in 40 ml toluene. The mixture was heated for an hour under reflux and cooled to room temperature. 100 ml Water was added carefully and the mixture acidified with 2N hydrochloric acid. The resulting precipitate was filtered and dried in vacuo. The resulting crude product was recrystallised from a chloroform/hexane mixture.

yield : 7.8 g (≡ 72% of theory)

m.p.: 122-123ºC

Example 2

1-[1-(3,5-Dichlorophenylaminocarbonyl)-1-methylethyl]-4-methoxy-3-(2-fluoro- phenyl)pyrrolin-2-one 4,0 g (9,5 mMol) 1-[1-(3,5-Dichlorophenylaminocarbonyl)-1-methylethyl]-4-hydroxy- 3-(2-fluorophenyl)pyrrolin-2-one was suspended in 20 ml acetonitrile and treated with 700 mg potassium hydroxide. A solution of 2.05 g (11 mMol) methyl

p-toluenesulfonate in 10 ml acetonitrile was added dropwise and the mixture heated under reflux for 3 hours. It was treated with 200 ml water and extracted three times each, with 50 ml methylene chloride. After drying and evaporating, there was obtained a solid foam. yield : 3.3 g (≡ 80% of theory)

Rf-value : 0.61 (EA) (EA = ethyl acetate) Example 3

1-[1-(3-Chlorophenylaminocarbonyl)-1-methylethyl]-4-methylamino-3-phenylpyrrolin- 2-one 1,3 g (3,5 mMol) 1-[1-(3-Chlorophenylaminocarbonyl)-1-methylethyl]-4-hydroxy- 3-phenylpyrrolin-2-oπe was dissolved in a mixture of 25 ml xylene and 4 ml acetic acid. 3.6 ml of a 40% methylamine solution was added with stirring and the reaction mixture heated under reflux for 4 hours with water removal. It was then treated with 100 ml ice/water and extracted three times each, with 50 ml methylene chloride. After drying and evaporating, there was obtained a solid foam,

yield : 1,3 g ( = 98% of theory)

m.p. : 95-100°C In a similar manner the following compounds of formula I were prepared (R² , R³ = H)

The following Examples illustrate the use of the compounds of the invention. In the Examples, the following abbreviations and scores are used

GLXMA Glycine max 0 = no damage

ZEAMX Zea mays 1 = 1-24 % damage

ALOMY Alopecurus myosuroides 2 = 25-74 % damage

GIGSA Digitaria sanguinalis 3 = 75-89 % damage

SETVI Setaria viridis 4 = 90-100 % damage

PANSS Panicum sp.

SORHA Sorghum halepense

ECHCG Echinochloa crus-galli

MATCH Matricaria chamomilla

VERPE Veronica persica Use Example A

The indicated plant species in the greenhouse were treated pre-emergence with the compounds in application amounts of 0.3 kg active ingredient/ha. For this purpose, the compounds were used as an emulsion with 500 litre water/ha and were sprayed uniformly over the soil. 2 weeks after treatment, the compounds according to the invention showed a high crop selectivity in wheat, maize and soya beans with excellent activity against the weeds.

Use Example B

In a greenhouse, the compound shown in the table were applied to a water surface of ca 170 cm² whereby the test plants both pre-emergence and in the 1-3 leaf stage

After two week the compounds of the invention showed strong activity against important rice weeds with good selectivity in paddy rice.

In the table

ai = active ingredient

Claims

1. 4-Hetero substituted pyrrolinone derivatives of general formula I

in which

R¹ is C₁ -C₆-alkyl, halo-C ₁-C₆-alkyl, C₁ -C₆-alkoxy-C₁ -C₆-alkyl or C₃-C₆-cycloalkyl, or phenyl, optionally substituted by the group X_m,

A is the group OR⁴, SR⁴, SOR⁴, SO₂R⁴ or NR⁵R⁶,

R² is hydrogen, C ₁-C₆-alkyl, C ₁-C₆-alkoxy, halogen, hydroxy, amino,

C ₁-C₆-alkylamino or C₁ -C₆-dialkylamino,

R³ is hydrogen, C₁ -C₆-alkyl or halogen,

R⁴ is hydrogen, C ₁-C₆-alkyl, halo-C ₁-C₆-alkyl, C ₁-C₆-alkoxy-C ₁-C₆-alkyl,

C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyI or C₃-C₆-cycloalkyl, or phenyl or benzyl, both of which are optionally substituted by the group X_m, or R⁴ is the group COR⁷,

R⁵ is hydrogen, C ₁-C₆-alkyl, halo-C₁ -C₆-alkyl, C₁ -C₆-alkoxy-C ₁-C₆-alkyl,

C ₁-C₆-alkoxy, C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl,

C₃-C₅-cycloalkyl or hydroxy, or phenyl or benzyl, both of which are optionally substituted by the group X_m, or R⁵ is the group COR⁷,

R⁶ is hydrogen, C ₁-C₆-alkyl, halo-C₁ -C₆-alkyl, C ₁-C₆-alkoxy-C₁ -C₆-alkyl,

C₂-C₆-aIkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₆-cycloalkyl, or phenyl or benzyl, both of which are optionally substituted by the group X_m, or R⁶ is the group COR⁷,

R⁷ is hydrogen, C ₁-C₆-alkyl, halo-C ₁-C₆-alkyl, C₆-C₆-cycloalkyl or phenyl, optionally substituted by the group X_m, X is hydrogen, hydroxy, C ₁-C₆-alkyl, halo-C ₁-C₆-alkyl, C ₁-C₆-alkoxy-C₁ -C₆-alkyl, C ₁-C₆-alkoxy, mercapto, C ₁-C₆-alkylthio, C ₁-C₆-alkylsulfonyl, C₁ -C₆-alkyl- sulfinyl, amino, C ₁-C₆-alkylamino, C₁ -C₆-dialkylamino, halogen, cyano, C ₁-C₆-alkoxycarbonyl, aminocarbonyl, C ₁-C₆-alkylaminocarbonyl,

C₁-C₆-dialkylaminocarbonyl or nitro,

m is 1, 2 or 3, whereby when m is 2 or 3 the substituent X can be the same or different,

E is the group -CO-R⁸ , the group

D is oxygen, sulfur, NH or N-C ₁-C₆-alkyl,

R⁸ is hydrogen, hydroxy, C₁ -C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkinyl or phenyl or benzyl, both of which are optionally substituted by the group X_m, or R⁸ is the group OR⁹, the group OM or the group NR¹⁰R^{1 1}

R⁹ is hydrogen, C ₁-C₆-alkyl, benzyl, phenyl or phenyl optionally substituted by

C₁ -C₆-alkyl, C₁ -C₆-alkoxy, halogen or nitro,

R¹⁰ is hydrogen, hydroxy, C₁ -C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, or

R^{1 1} is hydrogen, hydroxy, C ₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, or

C ₁-C₆-alkoxy, or phenyl or benzyl both of which are optionally substituted by the group X_m, R¹⁰ and R^{1 1} together with the nitrogen to which they are attached form a pyrrolidino, piperidino or morpholino group,

M is a cation selected from the group of lithium, sodium, potassium, one equivalent of from the group of zinc, manganese, calcium, barium or an ammonium ion.

2. 4-Hetero substituted pyrrolinone derivatives of general formula I, in

which

R¹ is phenyl, optionally substituted by the group X_m,

A is the group OR⁴, SO₂R^{4 or} NR⁵R⁶,

R² is hydrogen,

R³ is hydrogen,

R⁴ is hydrogen, C ₁-C₆-alkyl, halo-C₁ -C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl or the

group COR⁷,

R⁵ is hydrogen, C ₁-C₆-alkyl or phenyl, optionally substituted by the group X_m, R⁶ is hydrogen or C₁ -C₆-alkyl,

R⁷ is C₁ -C₆-alkyl,

X is halogen, C₁ -C₆-alkyl, C ₁-C₆-alkoxy, halo-C ₁-C₆-alkyl or cyano,

E is the group -CO-R⁸ or one of the substituents E-1 or E-6, each of which may be optionally substituted by C ₁-C₆-alkyl or phenyl,

D is sulfur or N-C ₁-C₆-alkyl,

R⁸ is hydroxy, C₁ -C₆-alkyl or the group NR¹⁰R^{1 1}

R10 is hydrogen and

R^{1 1} is phenyl, optionally substituted by the group X_m.

3. Herbicidal composition characterised by a content of at least one compound according to claim 1 or 2.

4. Herbicidal composition according to claim 3 in admixture with a carrier or adjuvant.

5. Use of compounds according to claims 1 or 2 for control of

monocotyledonous and dicotyledonous weeds.