DE19506202A1 - Herbicide compsns. contg. 3-phenyl uracil derivs. and urea deriv. - Google Patents

Abstract

Herbicide comprises at least one liquid and/or solid carrier, opt. additive(s) and: (a) an antagonistically effective amt. of 3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)-urea (A1) and/or 1-(1-methyl-1-phenylethyl)-3-(4-tolyl)-urea (A2); and (b) a herbicidally effective amt. of a 3-phenyl uracil (B).

Description

The present invention relates to new herbicidal compositions which at least one liquid and / or solid carrier, if desired, at least one adjuvant, and

• a) an antagonistically effective amount of 3- (2-chlorophenylme thyl) -1- (1-methyl-1-phenylethyl) urea and / or 1- (1-methyl-1-phenylethyl) -3- (4-tolyl) urea

and

• b) a herbicidally effective amount of at least one 3-phenyluracil

contain.

The invention also relates to processes for the production of these Means and methods for selective control of undesirable Plant growth on cultivated land.

Herbicidal 3-phenyluracils are generally well suited to treat harmful plants in stands of various crops fight. Your tolerance for dicot crops like Cotton, rapeseed, soy and sugar beet, but also for some grass like crops like barley, millet, corn, rice, wheat and However, sugar cane is not always sufficient, i. H. it in addition to the unwanted plants, the crop plants to an intolerably high degree with damage. One in general Desired reduction in the application rate has the disadvantage that The crops are spared, but at the same time the uninhabited desired plants are insufficiently controlled.

A method of using herbicidal 3-phenyluracils in the o.g. To enable cultures is to co-exist or at the same time with the herbicides one as "safener," antidote "or" anta gonist "to apply the second component, whereby the Damage to crops is reduced until it is completely avoided.

3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea and 1- (1-Methyl-1-phenylethyl) -3- (4-tolyl) urea were previously used as described herbicidally active compounds (see, for example, DE-A 42 09 475, JP-A 05/097 614, JP-A 05/177 118, JP-A 05/155 710, JP-A  05/155 720, JP-A 05/155 721, JP-A 05/139 920, JP-A 05/255 018 and U.S. 5,280,007).

In addition, various synergistic mixtures are made 3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea or 1- (1-methyl-1-phenylethyl) -3- (4-tolyl) urea and a second herbicidally active compound, e.g. B. a tetrahydrophthalimide (JP-A 49/050 137, JP-A 61/022 822), a diphenyl ether (JP-A 50/089 534, JP-A 56/166 104, JP-A 04/942 518) a tetrahydroin dazol (GB 2002 234) or an oxadiazolone (e.g. JP-A 56/166 104).

The object of the present invention was to be herbicidal compositions to put up a good control of unwanted plants guarantee, but without appreciably damaging the useful plants or significantly reduce their crop yield.

According to this task, the herbicides defined at the outset became Means found.

Furthermore, processes for the preparation of these agents and Process for the treatment of plant cultures with the antagoni active ureas and herbicidally active 3-phenylura cilen found, it is irrelevant whether the urea and the 3-phenyluracile formulated and worked out together or separately are brought and in what order the application at ge separate application.

In addition to the antagonistic and herbicidally active compounds other antagonistic or pesticidal substances be included.

The herbicidally active 3-phenyluracile, which has the following essential structural feature included

(R = hydrogen, amino, alkyl or haloalkyl)
are known, inter alia, from WO 89/30825; WO 89/02891; WO 90/15057; EP-A 542 685; WO 91/00278; EP-A 195 346; DE-A 42 37 920; EP-A 255 047; EP-A 260 621; EP-A 323 487; EP-A 344 232; EP-A 473 551; EP-A 563 384; EP-A 408 282; WO 92/11244; EP-A 489 480; EP-A 540 023; EP-A 5 517 181; WO 93/30319; EP-A 420 194, WO 93/06090; US 4,981,508 and US 4,979,982.

In particular, the herbicidal compositions comprise as component b) a 3-phenyluracil of the general formula I.

in which the substituents have the following meaning:
X¹, X² independently of one another oxygen or sulfur;
R1 halogen, cyano, trifluoromethyl or nitro;
R² is hydrogen or halogen;
R³ is hydrogen, amino, C₁-C₆ alkyl or C₁-C₆ haloalkyl;
R⁴ cyano, halogen, C₁-C₄ haloalkyl or C₁-C₄ alkyl;
R⁵ is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, (C₁-C₆-alkoxy) carbonyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or Phenyl;
R⁶ is a radical R⁷ or X³R⁷ or a saturated 5- to 7-membered heterocycle which, in addition to methylene units, contains one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as ring members, it being possible for the heterocycle to carry one or two radicals, each selected from the group consisting of cyano, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆ -Cyanoalkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl-C₁-C₆-alkyl, (C₁- C₆-alkyl) carbonyloxy-C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl;
or together with R¹ one of the following bridges - (R¹ ---- R⁶) -:
-O-CH₂-CO-NH-, -O-CO-NH-, -NH-CH₂-CO-NH-, -NH-CO-NH-, -N = CH-CO-NH- or -NH-CH = CH-, where one to three hydrogen atoms can be substituted independently of one another by one of the following radicals: halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyano alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbo nyl-C₁-C₆-alkyl, (C₁- C₆-alkyl) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyloxy-C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl;
R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alk oxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₁- C₆-alkyl thio-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbonyl-C₃-C₈-cycloalkyl, (C₁-C₆-alkyl) carbonyl- C₁-C₆-alkyl, (C₁-C₆-alkyl) carbo nyloxy-C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl;
X³ stands for oxygen, sulfur, carbonyl, -CO-O-, -CO-N (R⁸) -, -N (R⁸) -, -N (R⁸) -SO₂-, -SO₂-, -SO₂-O-, -SO₂-N (R⁸) -, -C (R⁹) = NO-, -C (R¹⁰) = C (R¹¹) -CO-X⁴-, -CH (R¹⁰) -CH (R¹¹) -CO-X⁴-, -C (R¹⁰) (OR⁸) -O-, -C (R¹⁰) (OR⁸) -S-, -C (R¹⁰) (SR⁸) -O- or -C (R¹⁰) (SR⁸) -S-, where
X⁴ oxygen, sulfur or -N (R⁸) -;
R⁸ hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alk oxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₁-C₆- Alkyl thio-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbo nyloxy-C₁ -C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl;
R⁹ hydrogen, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxy alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyloxy-C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl C₁-C₆-alkyl;
R¹⁰, R¹¹ independently of one another are hydrogen, cyano, halogen, C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl or (C₁-C₆-alkoxy) carbonyl;
mean.

Among the 3-phenyluracils I mentioned above, those compounds 1 are particularly preferred in which
R⁴ C₁-C₆ haloalkyl,
R⁵ is hydrogen, halogen or C₁-C₆ alkyl and
R⁶ X³R⁷ or or a saturated 5- to 7-membered heterocycle which, in addition to methylene units, contains one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as ring members, it being possible for the heterocycle to carry one or two radicals from the group consisting of cyano, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl , C₁-C₆-alkyl thio-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl ) carbonyl oxy-C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl
mean and X³ for -C (R⁹) = NO-, -C (R¹⁰) = C (R¹¹) -CO-X⁴-,
-CH (R¹⁰) -CH (R¹¹) -CO-X⁴-, -C (R¹⁰) (OR⁸) -O-,
-C (R¹⁰) (OR⁸) -S-, -C (R¹⁰) (SR⁸) -O- or
-C (R¹⁰) (SR⁸) -S- stands.

Herbicidal agents and antagonistic compounds can, together or separately, before or after the emergence of the Plant on the ground or on the leaves and shoots be brought. 3- (2-Chlorophenyl) is preferred methyl) -1- (1-methyl-1-phenylethyl) - and / or the 1- (1-Methyl-1-phenylethyl) -3- (4-tolyl) urea simultaneously with applied the herbicidal active ingredient. But it is also possible Antidote and herbicidal active ingredient separately on the field to brin gene.

There is still the possibility of the seeds or cuttings of the crop plants before sowing them or before planting them out 3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) - and / or to treat the 1- (1-methyl-1-phenylethyl) -3- (4-tolyl) urea deln, in which case the herbicidal active ingredient alone in is applied in the usual way.  

In the ready-to-use preparation, herbicide and antago is common in suspended, emulsified or dissolved form or formulated separately. Straighten the application forms depending on the intended use.

The agents according to the invention or - when applied separately the herbicidal active ingredients or the antidote - are for example wise in the form of directly sprayable solutions, powders, suspensions sions, also high-proof aqueous, oily or other Sus pensions, or dispersions, emulsions, oil dispersions, pastes, Dusts, sprinkles or granules by spraying, Nebulization, dusting, scattering or pouring applied.

For the production of directly sprayable solutions, emulsions, Pastes or oil dispersions are essentially considered: Mineral oil fractions from medium to high boiling point like Kero sin or diesel oil, as well as coal tar oils and vegetable oils or of animal origin, aliphatic, cyclic or aromatic cal hydrocarbons, e.g. B. toluene, xylenes, paraffins, tetra hydronaphthalene, alkylated naphthalenes or their derivatives, Al alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, Ketones such as cyclohexanone or strongly polar solvents, e.g. B. Amines such as N-methylpyrrolidone, or water.

Aqueous use forms can be obtained from emulsion concentrates, Sus pensions, pastes, wettable powders or water-dispersible Granules can be prepared by adding water. For the manufacture Emulsions, pastes or oil dispersions can be sub strate as such or dissolved in an oil or solvent, using wetting agents, adhesives, dispersants or emulsifiers in water be homogenized. But it can also be made from an active substance, Wetting, adhesive, dispersing or emulsifying agents and possibly Concentrates containing solvents or oil are produced, which are suitable for dilution with water.

The alkali, alkaline earth, Ammonium salts of aromatic sulfonic acids, e.g. B. lignin, Phenolic, naphthalene and dibutylnaphthalenesulfonic acid, as well as from Fatty acids, alkyl and alkyl aryl sulfonates, alkyl and lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and fatty alcohol glycol ethers, condensates products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxy ethylenoctylphenolether, ethoxylated isooctyl, octyl or Nonylphenol, alkylphenol, tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene  oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, Sorbitol ester, lignin sulfite liquor or methyl cellulose in Be dress.

Powders, materials for spreading and dusts can be mixed or mixed joint grinding of the active substances with a solid Carrier are manufactured.

Granules, e.g. B. wrapping, impregnation and homogeneous granules, by binding the active ingredients to solid carriers getting produced. Suitable carriers are e.g. B. mineral soils such as silicas, silica gels, silicates, talc, kaolin, Attaclay, Limestone, chalk, talc, bolus, loess, clay, dolomite, diatoms earth, calcium and magnesium sulfate, magnesium oxide, ground Plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate and ureas, vegetable products such as cereals flour, tree bark, wood and nutshell flour and cellulose powder.

The formulations contain between 0.1 and 95% by weight of compo nente a) {antidote} and b) {3-phenyluracil}, preferably between 0.5 and 90 wt%.

When the antidote is applied by swelling the semen or when Cuttings treatment are preferred solutions that at least one antagonistic agent in one concent tration of 1 to 10,000 ppm, in particular 100 to 10,000 ppm, contain.

The application rates of 3-phenyluracil (s) are 0.001 to 2 kg / ha, preferably 0.005 to 0.5 kg / ha. Depending on the respective crop and the herbicide used are un different amounts of antagonist are required. Appropriate share Relationship of component a) {antagonist} to component b) {3-phenyluracil} are generally 1:10 to 1: 0.01 parts by weight, with pre-emergence application in particular 1: 0.5 to 1: 0.05 Parts by weight, in the case of post-emergence treatment preferably 1: 4 to 1: 0.1 part by weight.

When treating seeds, amounts of active ingredient are generally used from 0.01 to 10 g, preferably 0.1 to 2 g, per kilogram of seed needed.

In addition to 3- (2-chlorophenylme thyl) -1- (1-methyl-1-phenylethyl) - and / or 1- (1-methyl-1-phenyl ethyl) -3- (4-tolyl) urea and at least one 3-phenyluracil  I other herbicidal or growth-regulating active ingredients of others chemical structure and, if desired, other plants contain protective agents.

Examples of biological effects

The influence of various representatives of the invention herbicidal compositions or combinations of compositions consisting of 3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea (Common name: cumyluron, dibenzyluron) or 1- (1-methyl-1-phenyl ethyl) -3- (4-tolyl) urea (common name: Dymron) and one herbicidally active 3-phenyluracil, on the growth of un wanted plants and crops compared to herbicidal Active ingredient alone is exemplified by the following crop house tests confirmed:

Plastic pots with around 300 cm³ were used for the greenhouse tests Content used as the loamy sand with about 3.0 wt% humus Contained substrate. The seeds of the potted plants were, according to Ar seperated, sown flat and moistened. In the pre-emergence process The floor surface in the pots was immediately connected ßend with aqueous preparations of the agents according to the invention sprayed.

For the post-emergence treatment, the test plants were Cultivated up to a height of 3 to 20 cm and then treated.

List of test plants

The two antagonistically active compounds were combined in one Mixture consisting of 80 wt .-% cyclohexanone as a diluent tel and 20 wt .-% surfactant (Emulphor EL 8-fold ethoxylated castor oil (Castor oil)) with 10 wt .-% active ingredient processed.  

The herbicidal 3-phenyluracils were as 10 to 20 wt .-% Emulsion concentrates in a solution of 93% by weight xylene and 7 % By weight Lutensol® AP-8 (non-ionic surfactant based on alkylphenol polyethylene glycol ethers).

Herbicide and antagonist were required in each Concentrations together with water to a spray mixture sets (tank mix).

After application of the respective active ingredient mixture using fine distributing nozzles, the test plants were cultivated in the greenhouse fourth, heat-loving species at about 18 to 30 ° C, such temperate climates at approx. 10 to 25 ° C.

The trial period lasted 3 to 5 weeks of which the plants were cared for. Then her re action on drug treatment recorded. Was rated in Comparison with the untreated control plants using a Scale from 0 to 100, with 0 no damage and 100 complete Destruction at least of the above-ground parts of the plants tet.

In Tables 1 to 4 below, the results are on culture plants from the family of the Graminen (grasses) and at Setaria viridis listed as representative of an important harmful plant:

Table 1

Improving the compatibility of a 3-phenyluracile (I with X¹, X² = oxygen, R¹ = chlorine, R² = fluorine, R³ = methyl, R⁴ = tri fluoromethyl, R⁵ = hydrogen and R⁶ = ethoxyiminomethyl) for maize or wheat by adding dymron or cumyluron at night Casserole application in the greenhouse:

Table 2

Improving the compatibility of a 3-phenyluracile (I with X¹, X² = oxygen, R¹ = chlorine, R² = fluorine, R³ = methyl, R⁴ = tri fluoromethyl, R⁵ = hydrogen and R⁶ = -CH = C (Cl) -CO-OC₂H₅ for wheat by adding cumyluron in post-emergence applications in the greenhouse

Table 3

Improving the compatibility of a 3-phenyluracile (I with X¹, X² = oxygen, R¹ = chlorine, R² = hydrogen, R³ = methyl, R⁴ = trifluoromethyl, R⁵ = hydrogen and R⁶ = -CH = NO-C (CH₃) -CO- OC₂H₅) for corn and wheat by adding Dymron in pre-emergence application in the greenhouse

Table 4

Improving the tolerance of a 3-phenyluracile (1 with X¹, X² = oxygen, R¹ = chlorine, R² = fluorine, R³ = methyl, R⁴ = trifluoromethyl, R⁵ = hydrogen and R⁶ = ethoxyiminomethyl) for corn and wheat by adding Dymron Pre-emergence application in the greenhouse

Claims (19)

1. Herbicidal compositions containing at least one liquid and / or solid carrier, if desired at least one adjuvant, and

• a) an antagonistically effective amount of 3- (2-chlorophenyl methyl) -1- (1-methyl-1-phenylethyl) urea and / or 1- (1-methyl-1-phenylethyl) -3- (4-tolyl )-urea
  and
• b) a herbicidally effective amount of at least one 3-phenyl uracil.

2. Herbicidal composition according to claim 1, containing as component b) a 3-phenyluracil of the general formula I. in which the substituents have the following meaning:
X¹, X² independently of one another oxygen or sulfur;
R1 halogen, cyano, trifluoromethyl or nitro;
R² is hydrogen or halogen;
R³ is hydrogen, amino, C₁-C₆ alkyl or C₁-C₆ haloalkyl;
R⁴ cyano, halogen, C₁-C₄ haloalkyl or C₁-C₄ alkyl;
R⁵ hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-halogeno alkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, (C₁-C₆-alkoxy) carbonyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or phenyl;
R⁶ is a radical R⁷ or X³R⁷ or a saturated 5- to 7-membered heterocycle which, in addition to methylenein, contains one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as ring members, the heterocycle being able to carry one or two radicals , each selected from the group consisting of cyano, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁- C₆-cyanoalkyl, C₁-C₆-Al kylthio-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbo nyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl-C₁-C₆-alkyl, (C₁ -C₆-alkyl) carbonyloxy-C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl;
or together with R¹ one of the following bridges - (R¹-R⁶) -: -O-CH₂-CO-NH-, -O-CO-NH-, -NH-CH₂-CO-NH-, -NH-CO-NH -, -N = CH-CO-NH- or -NH-CH = CH-, where one to three hydrogen atoms can be substituted independently of one another by one of the following radicals: halogen, cyano, C₁-C₆-alkyl, C₁-C₆ -Halogenalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₁-C₆-alkyl thio-C₁-C₆-alkyl, (C₁-C₆ -Alkoxy) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl oxy-C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃- C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl;
R⁷ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alk oxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₁- C₆-alkyl thio-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbo nyl-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbo nyl-C₃-C₈-cycloalkyl, (C₁-C₆-alkyl) carbo nyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl oxy-C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl;
X³ stands for oxygen, sulfur, carbonyl, -CO-O-, -CO-N (R⁸) -, -N (R⁸) -, -N (R⁸) -SO₂-, -SO₂-, -SO₂-O-, -SO₂-N (R⁸) -, -C (R⁹) = NO-, -C (R¹⁰) = C (R¹¹) -CO-X⁴-, -CH (R¹⁰) -CH (R¹¹) -CO-X⁴-, -C (R¹⁰) (OR⁸) -O-, -C (R¹⁰) (OR⁸) -S-, -C (R¹⁰) (SR⁸) -O- or -C (R¹⁰) (SR⁸) -S-, where
X⁴ oxygen, sulfur or -N (R⁸) -;
R⁸ hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alk oxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₁-C₆- Alkyl thio-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbo nyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbo nyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl oxy -C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl;
R⁹ hydrogen, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₁ -C₆-alkylthio-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyloxy- C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl;
R¹⁰, R¹¹ independently of one another are hydrogen, cyano, halo, C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl or (C₁-C₆-alkoxy) carbonyl;
mean. 3. A herbicidal composition according to claim 2, wherein
R⁴ C₁-C₆ haloalkyl,
R⁵ is hydrogen, halogen or C₁-C₆ alkyl and
R⁶ X³R⁷ or or a saturated 5- to 7-membered heterocycle which, in addition to methylene units, contains one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as ring members, it being possible for the heterocycle to carry one or two radicals, each selected from the group Group consisting of cyano, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyano alkyl, C₁-C₆-alkylthio-C _1- -C₆-alkyl, (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl) carbonyl-C₁-C₆-alkyl, (C₁-C₆- Alkyl) carbonyloxy-C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl
mean and X³ for -C (R⁹) = NO-, -C (R¹⁰) = C (R¹¹) -CO-X⁴-, -CH (R¹⁰) -CH (R¹¹) -CO-X⁴-, -C (R¹⁰) (OR⁸) -O-, -C (R¹⁰) (OR⁸) -S-, -C (R¹⁰) (SR⁸) -O- or -C (R¹⁰) (SR⁸) -S- is. 4. Herbicidal compositions according to claims 1 to 3, containing

• a) 3- (2-Chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea and / or 1- (1-methyl-1-phenylethyl) -3- (4-tolyl) urea
  and
• b) at least one 3-phenyluracil

in the weight ratio a): b) from 0.01: 1 to 10: 1. 5. Process for the preparation of herbicidally active agents, characterized in that

• a) an antagonistically effective amount of 3- (2-chlorophenyl-methyl) -1- (1-methyl-1-phenylethyl) urea and / or 1- (1-methyl-1-phenyl-ethyl) -3- (4-tolyl) urea
  and
• b) a herbicidally effective amount of at least one 3-phenyluracil

with at least one inert liquid and / or solid Carrier and, if desired, with at least one Adju vants mixes. 6. Process for the preparation of herbicidally active agents, characterized in that

• a) an antagonistically effective amount of 3- (2-chlorophenyl methyl) -1- (1-methyl-1-phenylethyl) urea and / or 1- (1-methyl-1-phenylethyl) -3- (4-tolyl ) urea and
• b) a herbicidally effective amount of at least one 3-phenyl uracil of the formula I according to claim 2,

with at least one inert liquid and / or solid Carrier and, if desired, with at least one Adju vants mixes. 7. Process for combating undesirable plant growth, characterized in that one

• a) an antagonistically effective amount of 3- (2-chlorophenyl methyl) -1- (1-methyl-1-phenylethyl) urea and / or 1- (1-methyl-1-phenylethyl) -3- (4-tolyl ) urea and
• b) a herbicidally effective amount of at least one 3-phenyl uracil

during or after sowing the crop, before or during or at the same time as the crops emerge spreads one after the other. 8. Process for combating undesirable plant growth, characterized in that one

• a) an antagonistically effective amount of 3- (2-chlorophenyl methyl) -1- (1-methyl-1-phenylethyl) urea and / or 1- (1-methyl-1-phenylethyl) -3- (4-tolyl ) urea and
• b) a herbicidally effective amount of at least one 3-phenyl uracil of the formula I according to claim 2,

during or after sowing the crop, before or during or at the same time as the crops emerge spreads one after the other. 9. A method for the selective control of undesirable plant growth, characterized in that the leaves of the crop plants and the undesirable plants in the after-emergence process

• a) an antagonistically effective amount of 3- (2-chlorophenyl methyl) -1- (1-methyl-1-phenylethyl) urea and / or 1- (1-methyl-1-phenylethyl) -3- (4-tolyl ) urea and
• b) a herbicidally effective amount of at least one 3-phenyl uracil

treated simultaneously or sequentially. 10. A method for the selective control of undesirable plant growth, characterized in that the leaves of the crop plants and the undesirable plants in the after-emergence process

• a) an antagonistically effective amount of 3- (2-chlorophenyl methyl) -1- (1-methyl-1-phenylethyl) urea and / or 1- (1-methyl-1-phenylethyl) -3- (4-tolyl ) urea and
• b) a herbicidally effective amount of at least one 3-phenyl uracil of the formula I according to claim 2,

treated simultaneously or sequentially. 11. Process for preventing crop damage by herbicidally active 3-phenyluracil, characterized net that the seeds of the crop plants with an antago  effective amount of 3- (2-chlorophenylme thyl) -1- (1-methyl-1-phenylethyl) urea and / or 1- (1-Methyl-1-phenylethyl) -3- (4-tolyl) urea treated. 12. The method according to claims 7 to 11, characterized in net that the crops rice, wheat, corn, barley, millet and cane are.