Substituted nitroanilines and ureas as herbicidal mixtures

Abstract

Herbicidal mixtures useful as selective herbicides embodying 2,4,6-trisubstituted anilines, at least one substituent being nitro, and substituted ureas in a weight ratio of 1:3 to 3:1.

Description

The present invention relates to herbicides, particularly selective herbicides, which are suitable for controlling the growth of unwanted plants in crop plants.

It is known to use substituted dinitroaniline derivatives, phosphoric acids, pyridazones, substituted ureas, triazines and biscarbamates as herbicidal active ingredients. However, their action is not always satisfactory.

I have now found that herbicides comprising a mixture of

A. A COMPOUND OF THE FORMULA ##SPC1##

Where R.sup.1 denotes hydrogen, nitro, alkyl, trifluoromethyl or methylsulfonyl, R.sup.2 denotes nitro, alkyl, trifluoromethyl or methylsulfonyl, R.sup.3 and R.sup.4 are identical or different and denote hydrogen, a linear or branched, saturated or unsaturated aliphatic radical which may be substituted by halogen, cyano, alkoxy or azido, or haloacetyloxyalkyl or alkylcarbamoyloxyalkyl, and R.sup.3 and R.sup.4, together with the nitrogen atom whose substituents they are, may also form a hexamethylenimine ring, with

B. A COMPOUND OF THE FORMULA ##SPC2##

Where R denotes phenyl which may be substituted by halogen, nitro, alkyl, alkoxy, alkenoxy, alkynoxy, haloalkyl, alkyl or dialkylcarbamoyloxy, a cycloaliphatic, bicycloaliphatic or tricycloaliphatic radical which may be substituted by halogen or alkyl, 3-benzothiazoly substituted or unsubstituted phenoxyalkyl, alkenyl or alkynylcarbamoyoxy, R.sup.1 denotes hydrogen, cyclooctenyl or cyclohexenyl, R.sup.2 denotes hydrogen, alkyl, alkoxy, alkoxyalkyl, isobuten-(1)-yl-3, .alpha.,.alpha.-dimethylpropargyl, cyanoalkyl, or carboxyalkyloxy, R.sup.2 further denotes an alkyl ##STR1## radical or its salts or esters, have a good herbicidal action, both pre- and postemergence, on weeds such as Chenopodium album, Galinsoga parviflora, Sinapis arvensis, Polygonum spp., Amaranthus spp., and Portulaca oleracea; on grassy weeds such as Poa spp., Bromus spp., Avena sativa and Cyperus spp.; and on millet types such as Panicum spp., Setaria spp., Digitaria spp., and Echinochloa spp. in the following crops: Gossypium spp., Soja hispida, Brassica napus, Beta spp., and Oryza sativa.

The individual active ingredients may be mixed together in any desired ratio; however, mixtures in which the ratio by weight of a to b compounds above is from 3:1 to 1:3 are preferred.

The agents according to the invention may be used as solvents, emulsions, suspensions or dusts. The form of application depends entirely on the purpose for which the agents are being used; in any case it should ensure a fine distribution of the active ingredient.

For the preparation of solutions to be sprayed direct, hydrocarbons having boiling points higher than 150.degree. C, e.g. tetrahydronaphthalene or alkylated naphthalenes, or organic liquids having boiling points higher than 150.degree. C and having one or more than one functional group, e.g. the keto group, the ether group, the ester group or the amide group, this group or these groups being attached as substituent(s) to a hydrocarbon chain or being a component of a heterocyclic ring, may be used as spray liquids.

Aqueous formulations may be prepared from emulsion concentrates, pastes or wettable powders by adding water. To prepare emulsions the ingredients as such or dissolved in a solvent may be homogenized in water or organic solvents by means of wetting or dispersing agents, e.g. polyethylene oxide adducts. Concentrates which are suitable for dilution with water may be prepared from active ingredient, emulsifying or dispersing agent and possibly solvent.

Dusts may be prepared by mixing or grinding the active ingredients with a solid carrier, e.g. kieselguhr, talc, clay or fertilizers.

To improve the action, wetting agents and adhering agents or oils may also be added.

EXAMPLE 1

An agricultural plot was sown with Gossupium hirsutum, Setaria viridis, Echinochloa crus-galli, Bromus tectorum, Amaranthus retroflexus and Portulaca oleracea and subsequently treated with the following amounts of the following individual active ingredients and mixtures of them, each active ingredient and each mixture being emulsified or dispersed in 500 liters of water per hectare:

I n-allyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline, 1.5 and 4 kg per hectare; Ii n-propyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline, 1 and 4 kg per hectare; Iii n-propyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline, 2 and 4 kg per hectare; Iv n-ethyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline, 2 and 3 kg per hectare; V n,n-dipropyl-2,6-dinitro-4-methylsulfonylaniline, 1.5 and 3 kg per hectare; Vi n-m-trifluoromethylphenyl-N-1-cyclohex-1-enyl-N',N-40 -dimethylurea, 2.5 and 4 kg per hectare; Vii n-m-chlorophenyl-N-1-cyclohex-1-enyl-N',N-40 -dimethylurea, 3 and 4 kg per hectare; Viii n-p-fluorophenyl-N-1-cyclohex-1-enyl-N-methylurea, 2 and 4 kg per hectare; Ix n-m-trifluoromethylphenyl-N',N'-dimethylurea, 1.5 and 3 kg per hectare; X n-p-chlorophenyl-N',N'-dimethylurea, 1 and 3 kg per hectare; I + vi : 1.5 + 2.5 kg per hectare; Ii + vii : 1 + 3 kg per hectare; Iii + viii: 2 + 2 kg per hectare; Iv + x : 2 + 1 kg per hectare; V + ix : 1.5 + 1.5 kg per hectare.

After 4 to 5 weeks it was ascertained that the mixtures had a stronger herbicidal action than the individual active ingredients, combined with more favorable crop plant compatibilty.

The results of the experiment are given in the following table:

Table__________________________________________________________________________ I II III IV V VI VII VIII IX Xkg/ha 1.5 4 1 4 2 4 2 3 1.5 3 2.5 4 3 4 2 4 1.5 3 1 3__________________________________________________________________________Gossypium hirsutum 0 15 0 30 0 20 0 20 0 15 0 35 0 10 0 30 0 20 30Setaria viridis 90 100 55 100 60 95 80 100 80 100 80 100 70 90 70 100 60 95 70 100Echinochloa 80 60 55 100 60 95 80 100 80 100 95 100 70 90 80 100 60 95 70 100crus-galliBromus tectorum 80 100 50 100 70 80 60 75 70 95 70 100 70 95 70 100 75 90 60 100Amaranthus retro- 80 60 25 80 20 50 25 40 20 45 90 100 80 100 80 100 70 100 80 100flexusPortulaca oleracea 30 80 25 75 35 55 30 50 30 60 100 100 80 100 80 100 80 100 80 100 I + VI II + VII III + VIII IV + X V + IXkg/ha 1.5 + 2.5 1 + 3 2 + 2 2 + 1 1.5 + 1.5__________________________________________________________________________Gossypium hirsutum 0 0 0 0 0Setaria viridis 100 100 100 100 100Echinochloa crus-galli 100 100 100 100 100Bromus tectorum 100 100 100 100 100Amaranthus retroflexus 100 100 100 100 100Portulaca oleracea 100 100 100 100 100__________________________________________________________________________ 0 = no damage 100 = complete destruction

The action of the following mixtures corresponds to that of the mixtures in Example 1:

N,n-dipropyl-2,6-dinitro-4-trifluoromethylaniline; N-.beta.-methoxyethyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline; N-.beta.-methoxyethyl-N-.beta.-azidoethyl-2,6-dinitro-4-trifluoromethylaniline; N-ethyl-N-butyl-2,6-dinitro-4-trifluoromethylaniline; N-isobutyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-ethyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-methyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-butyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-.beta.-methyoxyethyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-methyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-butyl-N-.beta.-chloropropyl-2,6-dinitro-4-trifluoromethylaniline; N-butyl-N-.beta.-chloropropyl-2,6-dinitro-4-trifluoromethylaniline; N-propyl-N-.beta.-chloropropyl-2,6-dinitro-4-trifluoromethylaniline; N-propyl-N-.beta.-bromoethyl-2,6-dinitro-4-trifluoromethylaniline; N,n-bis-.beta.-(chloroethyl)-2,6-dinitro-4-trifluoromethylaniline; N,n-bis-.beta.-(chloroethyl)-2,6-dinitro-4-methylaniline; N-propyl-N-allyl-4,6-dinitro-2-trifluoromethylaniline; N-ethyl-N-.beta.azidoethyl-2,6-dinitro-4-trifluoromethylaniline; N-propyl-N-.beta.-azidoethyl-2,6-dinitro-4-trifluoromethylaniline; N-propyl-N-.beta.-(chloroacetyloxy)-ethyl-2,6-dinitro-4-trifluoromethylaniline; N,n-bis-(.beta.-chloroacetyloxy)-ethyl-2,6-dinitro-4-trifluoromethylaniline N-(.beta.-chloroacetyloxy)-ethyl-2,6-dinitro-4-trifluoromethylaniline; N-(.beta.-methylcarbamoyloxy)-ethyl-2,6-dinitro-4-trifluoromethylaniline; N-ethyl-N-.beta.-bromoethyl-2,6-dinitro-4-trifluoromethylaniline; N-.beta.-methoxyethyl-N-.beta.-bromoethyl-2,6-dinitro-4-trifluoromethylaniline; N-.delta.-chloropropyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline; N-propen-(1)-yl-(3)-N-.beta.-chloroethyl-2,6-dinitro-4-methylaniline; N-propyl-N-.beta.-chloroethyl-2,6-dinitro-4-methylaniline; N-propyl-N-.beta.-azidoethyl-2,6-dinitro-4-methylaniline; N-propyl-N-.beta.-azidoethyl-2,6-dinitro-4-methylsulfonylaniline; N-propyl-N-.beta.-bromoethyl-2,6-dinitro-4-methylsulfonylaniline; N-propyl-N-.beta.-(chloroacetyloxy)-ethyl-2,6-dinitro-4-methylaniline; N-propyl-N-.beta.-(chloroacetyloxy)-propyl-2,6-dinitro-4-trifluoromethylaniline; or N-propyl-N-.beta.-(methylcarbamoyloxy)-propyl-2,6-dinitro-4-trifluoromethylaniline; with N-m-trifluoromethylphenyl-N-cyclohex-1-enyl-N'-methylurea; N-3-chlorophenyl-N-cyclohex-1-enyl-N'-methylurea; N-3-chloro-4-methoxyphenyl-N-cyclohex-1-enyl-N'-methylurea; N-4-chlorophenyl-N-cyclohex-1-enyl-N'-methylurea; N-phenyl-N-cyclohex-1-enyl-N'-methylurea; N-phenyl-N-cyclohex-1-enyl-N'N'-dimethylurea; 1-(m-tert-butylcarbamoyloxyphenyl)-3-methylurea; 1-(m-ethylcarbamoyloxyphenyl)-3-methylurea; 1-(m-allyl-tert-butylcarbamoyloxyphenyl)-3,3-dimethylurea; 1-(m-.alpha.,.alpha.-dimethylpropyn-(1)-yl-(3)carbamoyloxyphenyl)-3-methyl-3-methoxyurea; 1-(m-.alpha.-methyl-.alpha.-ethylpropyn-(1)-yl-(3)carbamoyloxyphenyl)-3-methyl-3-methoxyurea; 1-(m-tert-butylallylcarbamoyloxyphenyl)-3-methyl-3-methoxyurea; N-m-trifluoromethylphenyl-N'-butyn-(1)-yl-(3)-urea; N-3-chloro-4-methoxyphenyl-N'-methyl-N'-methoxyurea; N-m-trifluoromethylphenyl-N-methoxymethyl-N'-methylurea; N-m-trifluoromethylphenyl-N-methoxymethyl-N'-methyl-N'-methoxyurea; N-m-trifluoromethylphenyl-N-acetyloxymethyl-N',N'-dimethylurea; N-4-bromophenyl-N-cyclohex-1-enyl-N'N'-dimethylurea; N-3,4-dichlorophenyl-N-cyclohex-1-enyl-N'N'-dimethylurea; N-3-chloro-4-methoxyphenyl-N-cyclohex-1-enyl-N'N'-dimethylurea; N-[1- or 2-(3a, 4, 5, 6, 7,7a-hexahydro)-4-methanoindanyl]-N'N'-dimethyl-N-cyclohex-1-enylurea; N-m-trifluoromethylphenyl-N-cyclooct-1-enyl-N'N'-dimethylurea; N-m-trifluoromethylphenyl-N-cyclooctyl-1-enyl-N'-methylurea; N- 5-(3a,4,5,6,7,7a-hexahydro-4-methanoindanyl-N'N'-dimethylurea; N- 1- or 2-(3a,4,5,6,7,7a-hexahydro)-4-methanoindanyl-N'N'-dimethylurea; N-bicyclo-(3,3,0)-octyl-N'N'-dimethylurea; N-3,4-dichlorophenyl-N'N'-dimethylurea; N-cyclooctyl-N'N'-dimethylurea; or N-m-dimethylcarbamoyloxyphenyl-N'-methylurea.

EXAMPLE 2

An agricultural area was sown with Soja hispida, Digitaria sanguinalis, Bromus tectorum, Amaranthus retroflexus and Portulaca oleracea and subsequently treated with the following amounts of the following individual active ingredients and mixtures of them, each active ingredient and each mixture being dispersed or emulsified in 500 liters of water per hectare:

I n-allyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline, 1 and 3 kg per hectare; Ii n-propyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline, 1 and 2 kg per hectare; Iii n',n-dipropyl-2,6-dinitro-4-trifluoromethylaniline, 1 and 3 kg per hectare; Iv 1-m-trifluoromethyl-4-dimethylamino-5-chloropyridazone-6, 2 and 3 kg per hectare; V 1-phenyl-4,5-dimethoxypyridazone-6, 1 and 2 kg per hectare; Vi 1-m-methylphenyl-4-methoxy-5-bromopyridazone-6, 2 and 3 kg per hectare; Vii n-m-trifluoromethylphenyl-N-cyclohex-1-enyl-N',N'-dimethylurea; 2 and 3 kg per hectare; Viii n,n-dimethyl-N'-[N"-methoxyisopropylcarbamoyloxyphenyl]-urea, 1 and 2 kg per hectare; Ix n-4-(p-chlorophenoxy)-phenyl-N',N-dimethylurea, 2 and 3 kg per hectare; X 2-chloro-4-ethylamino-6-(.alpha.,.alpha.-dimethylcyanomethyl)-amino-1,3,5-triazine, 1 and 2 kg per hectare; I + iv : 1 + 2 kg per hectare; Ii + v : 1 + 1 kg per hectare; Iii + vi : 1 + 2 kg per hectare; I + vii : 1 + 2 kg per hectare; Ii + viii : 1 + 1 kg per hectare; Iii + ix : 1 + 2 kg per hectare; Ii + x : 1 + 1 kg per hectare.

After 4 to 5 weeks it was ascertained that the mixtures had a stronger herbicidal action than the individual active ingredients, combined with more favorable crop plant compatibility.

The results of the experiment are given in the following table:

Table__________________________________________________________________________ I II III IV V VI VII VIII IX Xkg/ha 1 3 1 2 1 3 2 3 1 2 2 3 2 3 1 2 2 3 1 2__________________________________________________________________________Soja hispida 0 15 0 10 0 20 0 15 0 20 0 10 0 20 0 20 5 25 20Digitaria sanguinalis 70 100 85 100 70 100 65 95 55 90 50 75 80 100 45 85 60 90 30 75Bromus tectorum 70 100 75 100 70 100 55 80 55 95 40 65 50 75 50 95 55 80 50 95Amaranthus 15 50 25 50 15 50 60 85 70 100 70 95 90 100 50 95 45 90 45 85retroflexusPortulaca oleracea 15 50 25 55 20 55 60 85 70 95 65 90 95 100 65 100 60 95 70 100 I + IV II + V III + VI I + VII II + VIII III + II + Xkg/ha 1 + 2 1 + 1 1 + 2 1 + 2 1 + 1 1 + 2 1 + 1__________________________________________________________________________Soja hispida 0 0 0 0 0 0 0Digitaria sanguinalis 100 100 100 100 100 100 100Bromus tectorum 100 100 100 100 100 100 100Amaranthus retroflexus 85 100 95 100 90 80 85Portulaca oleracea 90 100 100 100 100 95 100__________________________________________________________________________ 0 = no damage 100 = complete destruction

The action of the following mixtures corresponds to that of those above:

N-.beta.-methoxyethyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline; N-.beta.-methoxyethyl-N-.beta.-azidoethyl-2,6-dinitro-4-trifluoromethylaniline; N-propyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-ethyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline; N-ethyl-N-butyl-2,6-dinitro-4-trifluoromethylaniline; N-isobutyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-ethyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-methyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-.beta.-methoxyethyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-butyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-methyl-N-.beta.-cyanoethyl-2,6-dinitro-4-trifluoromethylaniline; N-butyl-N-.beta.-chloropropyl-2,6-dinitro-4-trifluoromethylaniline; N-isobutyl-N-.gamma.-chloropropyl-2,6-dinitro-4-trifluoromethylaniline; N-propyl-N-.beta.-chloropropyl-2,6-dinitro-4-trifluoromethylaniline; N-propyl-N-.beta.-bromoethyl-2,6-dinitro-4-trifluoromethylaniline; N,n-bis-.beta.-(chloroethyl)-2,6-dinitro-4-trifluoromethylaniline; N,n-bis-.beta.-(chloroethyl)-2,6-dinitro-4-methylaniline; N-propyl-N-allyl-4,6-dinitro-2-trifluoromethylaniline; N-ethyl-N-.beta.-azidoethyl-2,6-dinitro-4-trifluoromethylaniline; N-propyl-N-.beta.-azidoethyl-2,6-dinitro-4-trifluoromethylaniline; N-propyl-N-.beta.-(chloroacetyloxy)-ethyl-2,6-dinitro-4-trifluoromethylaniline; N,n-bis-(.beta.-chloroacetyloxy)-ethyl-2,6-dinitro-4-trifluoromethylaniline N-(.beta.-chloroacetyloxy)-ethyl-2,6-dinitro-4-trifluoromethylaniline; N-(.beta.-methylcarbamoyloxy)-ethyl-2,6-dinitro-4-trifluoromethylaniline; N-ethyl-N-.beta.-bromoethyl-2,6-dinitro-4-trifluoromethylaniline; N-.beta.-methoxyethyl-N-.beta.-bromoethyl-2,6-dinitro-4-trifluoromethylaniline; N-.gamma.-chloropropyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline; N-propen-(1)-yl-(3)-N-.beta.-chloroethyl-2,6-dinitro-4-methylaniline; N-propyl-N-.beta.-chloroethyl-2,6-dinitro-4-methylaniline; N-propyl-N-.beta.-azidoethyl-2,6-dinitro-4-methylaniline; N-propyl-N-.beta.-azidoethyl-2,6-dinitro-4-methylsulfonylaniline; N-propyl-N-.beta.-bromoethyl-2,6-dinitro-4-methylsulfonylaniline; N-propyl-N-.beta.-(chloroacetyloxy)-ethyl-2,6-dinitro-4-methylaniline; N-propyl-N-.beta.-(chloroacetyloxy)-propyl-2,6-dinitro-4-trifluoromethylaniline; or N-propyl-N-.beta.-(methylcarbamoyloxy)-propyl-2,6-dinitro-4-trifluoromethylaniline with 1-(m-tert-butylcarbamoyloxyphenyl)-3-methylurea; 1-(ethylcarbamoyloxyphenyl)-3-methylurea; 1-(m-allyl-tert-butylcarbamoyloxyphenyl)-3,3-dimethylurea; 1-(m-.alpha.,.alpha.-dimethylpropyn-(1)-yl-(3)carbamoyloxyphenyl)-3-methyl-3-methoxyurea; 1-(m-.alpha.-methyl-.alpha.-ethylpropyn(1)-yl-(3)carbamoyloxyphenyl)-3-methyl-3-methoxyurea; 1-(m-tert-butylallylcarbamoyloxyphenyl)-3-methyl-3-methoxyurea; N-m-trifluoromethylphenyl-N'-methyl-N'-butyn-(1)yl(3)-urea; N-3-chloro-4-methoxyphenyl-N'-methyl-N'-methoxyurea; N-m-trifluoromethylphenyl-N-methoxymethyl-N'-methylurea; N-m-trifluoromethylphenyl-N-methoxymethyl-N'-methyl-N'-methoxyurea; N-m-trifluoromethylphenyl-N-acetyloxymethyl-N',N'-dimethylurea; N-m-trifluoromethylphenyl-N-cyclohex-1-enyl-N'-methylurea; N-3-chlorophenyl-N-cyclohex-1-enyl-N'-methylurea; N-3-chloro-4-methoxyphenyl-N-cyclohex-1-enyl-N'-methylurea; N-4-chlorophenyl-N-cyclohex-1-enyl-N'-methylurea; N-phenyl-N-cyclohex-1-enyl-N'-methylurea; N-phenyl-N-cyclohex-1-enyl-N'N'-dimethylurea; N-4-bromophenyl-N-cyclohex-1-enyl-N'N'-dimethylurea; N-3,4-dichlorophenyl-N-cyclohex-1-enyl-N'N'-dimethylurea; N-3-chloro-4-methoxyphenyl-N-cyclohex-1-enyl-N'N'-dimethylurea; N-[1- or 2- (3a,4,5,6,7,7a-hexahydro-4)-methanoindanyl]-N'N'-dimethyl-N-cyclohex-1-enylurea; N-m-trifluoromethylphenyl-N-cyclooct-1-enyl-N'N'-dimethylurea; N-m-trifluoromethylphenyl-N-cyclooctyl-1-enyl-N'-methylurea; N-[5-(3a,4,5,6,7,7a-hexahydro-4)-methanoindanyl]-N'N'-dimethylurea; N-[1- or 2-(3a,4,5,6,7,7a-hexahydro-4-)-methanoindanyl]-N'N'-dimethylurea; N-bicyclo-(3,3,0)-octyl-N'N'-dimethylurea; N-3,4-dichlorophenyl-N'N'-dimethylurea; N-cyclooctyl-N'N'-dimethylurea; N-m-dimethylcarbamoyloxyphenyl-N'-methylurea; N-p-chlorophenyl-N-1-cyclohex-1-enyl-N'N'-dimethylurea; N-p-fluorophenyl-N-1-cyclohex-1-enyl-N'-methylurea; N-4-[4-methoxyphenoxyphenyl]-N'N'-dimethylurea; N-3,4-dichlorophenyl-N'-methyl-N'-methoxyurea; N-(3-chloro-4-bromophenyl)-N'-methyl-N'-methoxyurea;

As further examples of the synergistic action of the subject substituted anilines and substituted ureas, the following herbicidal experiments were conducted.

EXAMPLE 3

Experiment A

In the greenhouse I filled loamy sandy soil into pots and sowed it with seeds of the plants listed below. I then treated the soil prepared in this manner with the following amounts of the following individual active ingredients and mixtures thereof in the form of emulsions or dispersions:

I n-propyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline, 0.25, 0.5, 0.75 and 1 kg per hectare Ii n-3-trifluoromethylphenyl-N-cyclohex-1-enyl-N',N'-dimethylurea 0.25, 0.5, 0.75 and 1 kg per hectare Iii n-3,4-dichlorophenyl-N',N'-dimethylurea, 0.25, 0.5, 0.75 and 1 kg per hectare Iv n-[5-(3a,4,5,6,7,7a-hexahydro-4,7-methanoindanyl)]-N',N'-dimethylurea, 0.25, 0.5, 0.75 and 1 kg per hectare V n-[1- or 2-(3a,4,5,6,7,7a-hexahydro-4,7-methanoindanyl)]-N',N'-dimethylurea, 0.25, 0.5, 0.75 and 1 kg per hectare Vi n-3,4-dichlorophenyl-N'-methyl-N'-methoxyurea, 0.25, 0.5, 0.75 and 1 kg per hectare. I + ii: 0.25 + 0.75, 0.75 + 0.25, and 0.5 + 0.5 kg per hectare I + iii: 0.25 + 0.75, 0.75 + 0.25, and 0.5 + 0.5 kg per hectare I + iv: 0.25 + 0.75, 0.75 + 0.25, and 0.5 + 0.5 kg per hectare I + v: 0.25 + 0.75, 0.75 + 0.25, and 0.5 + 0.5 kg per hectare I + vi: 0.25 + 0.75, 0.75 + 0.25, and 0.5 + 0.5 kg per hectare After 4 to 5 weeks it was ascertained that the mixtures had a better herbicidal action than the sum of the actions of their individual components, combined with the same good crop plant compatibility.

The results of this experiment are given below:

Table__________________________________________________________________________Active ingredient I II III IVkg/ha 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.0__________________________________________________________________________Crop plantsGossypium hirsutum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Soja hispida 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Unwanted plantsDigitaria sanguinalis 25 45 60 85 20 35 50 60 24 40 54 65 25 45 55 70Echinochloa crus galli 32 50 58 70 18 30 40 50 20 32 50 60 28 45 65 90Lamium amplexicaule 0 0 0 5 30 55 70 80 35 58 75 85 10 20 25 35__________________________________________________________________________ 0 = no damage 100 = complete destruction Table__________________________________________________________________________Active ingredient V VI I + IIkg/ha 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.0 0.25 + 0.75 0.75 + 0.25 0.5 + 0.5__________________________________________________________________________Crop plantsGossypium hirsutum 0 0 0 0 0 0 0 0 0 0 0 0 0 0Soja hispida 0 0 0 0 0 0 0 0 0 0 0 0 0 0Unwanted plantsDigitaria sanguinalis 30 45 60 90 20 40 58 70 100 100 100Echinochloaccrus galli 25 48 65 90 25 45 60 70 100 100 100Lamium amplexicaule 5 15 20 25 30 50 70 80 100 178 97__________________________________________________________________________ 0 = no damage 100 = complete destruction Table__________________________________________________________________________Active ingredient I + III I + IV I + Vkg/ha 0.25+0.75 0.75+0.25 0.5+0.5 0.25+0.75 0.75+0.75 0.5+0.5 0.25+0.75 0.75+0.25__________________________________________________________________________Crop plantsGossypium hirsutum 0 0 0 0 0 0 0 0Soja hispida 0 0 0 0 0 0 0 0Unwanted plantsDigitaria sanguinalis 100 100 100 100 100 100 100 100Echinochloa crus galli 100 100 100 100 100 100 100 100Lamium amplexicaule 100 82 100 70 60 65 68 60__________________________________________________________________________ 0 = no damage 100 = complete destruction Table______________________________________Active ingredient I + VIkg/ha 0.25+0.75 0.75+0.25 0.5+0.5______________________________________Crop plantsGossypium hirsutum 0 0 0Soja hispida 0 0 0Unwanted plantsDigitaria sanguinalis 100 100 100Echinochloa crus galli 100 100 100Lamium amplexicaule 100 80 95______________________________________ 0 = no damage 100 = complete destruction

EXPERIMENT B

An agricultural plot was sown with seeds of the plants listed below. The soil was then immediately treated with the following amounts of the following individual active ingredients and mixtures thereof in the form of emulsions or dispersions:

I n-propyl-N-(2'-chloroethyl)-2,6-dinitro-4-trifluoromethylaniline, 0.25, 0.5, 0.75 and 1.0 kg per hectare Ii n-(2-benzothiazolyl)-N-methyl-N'-methylurea, 0.25, 0.5, 0.75 and 1.0 kg per hectare Iii n-(3-chloro-4-methylphenyl)-N',N'-dimethlurea, 0.25, 0.5, 0.75 and 1.0 kg per hectare Iv n-(3-trifluoromethylphenyl)-N',N'-dimethylurea, 0.25, 0.5, 0.75 and 1.0 kg per hectare V n-(3-chloro-4-methoxyphenyl)-N',N'-dimethylurea, 0.25, 0.5, 0.75 and 1.0 kg per hectare Vi n-(3-chloro-4-methoxyphenyl)-N'-methyl-N'-methoxyurea, 0.25, 0.5, 0.75 and 1.0 kg per hectare Vii n-(3-chloro-4-methoxyphenyl)-N-cyclohex-1-enyl-N',N'-dimethylurea, 0.25, 0.5, 0.75 and 1.0 kg per hectare Viii n-(3-chloro-4-methylphenyl)-N-cyclohex-1-enyl-N',N'-dimethylurea, 0.25, 0.5, 0.75 and 1.0 kg per hectare. I + ii : 0.75 + 0.25, 0.5 + 0.5 and 0.25 + 0.75 kg per hectare I + iii: 0.75 + 0.25, 0.5 + 0.5 and 0.25 + 0.75 kg per hectare I + iv : 0.75 + 0.25, 0.5 + 0.5 and 0.25 + 0.75 kg per hectare I + v : 0.75 + 0.25, 0.5 + 0.5 and 0.25 + 0.75 kg per hectare I + vi : 0.75 + 0.25, 0.5 + 0.5 and 0.25 + 0.75 kg per hectare I + vii: 0.75 + 0.25, 0.5 + 0.5 and 0.25 + 0.75 kg per hectare I + viii: 0.75 + 0.25, 0.5 + 0.5 and 0.25 + 0.75 kg per hectare After 3 to 4 weeks it was ascertained that the mixtures had a better herbicidal action than the sum of the actions of their individual components, combined with the same good crop plant compatibility.

The results of this experiment are given below:

Table__________________________________________________________________________Active ingredient I II III IVkg/ha 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.0__________________________________________________________________________Crop plantsTriticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Gossypium hirsutum 0 0 0 0 -- -- -- -- -- -- -- -- 0 0 0 0Unwanted plantsAlopecurus myosuroides 23 41 50 63 10 18 25 35 10 20 30 40 14 26 45 53Stellaria media 5 7 10 16 15 35 53 70 20 43 63 85 19 42 64 80__________________________________________________________________________ 0 = no damage 100 = total destruction Table__________________________________________________________________________Active ingredient V VI VII VIIIkg/ha 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.0__________________________________________________________________________Crop plantsTriticum pestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Gossypium hirsutum -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- --Unwanted plantsAlopecurus myosuroides 15 28 40 50 16 35 50 75 10 20 31 40 15 32 48 60Stellaria media 17 37 51 75 18 36 53 70 13 27 43 50 11 25 36 50__________________________________________________________________________ 0 = no damage 100 = complete destruction Table__________________________________________________________________________Active ingredient I + II I + III I + IVkg/ha 0.25+0.75 0.5+0.5 0.75+0.25 0.25+0.75 0.5+0.5 0.75+0.25 0.25+0.75 0.5+0.5 0.75+0.25__________________________________________________________________________Crop plantsTriticum aestivum 0 0 0 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0 0 0 0Gossypium hirsutum -- -- -- -- -- -- 0 0 0Unwanted plantsAlopecurus myosuroides 78 88 90 85 95 91 96 100 95Stellaria media 90 70 57 95 82 62 100 80 63__________________________________________________________________________ 0 = no damage 100 = complete destruction Table__________________________________________________________________________Active ingredient I + V I + VIkg/ha 0.25+0.75 0.5+0.5 0.75+0.25 0.25+0.75 0.5+0.5 0.75+0.25__________________________________________________________________________Crop plantsTriticum aestivum 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0Gossypium hirsutum -- -- -- -- -- --Unwanted plantsAlopecurus myosuroides 90 98 97 100 100 95Stellaria media 88 75 60 90 75 60__________________________________________________________________________ 0 = no damage 100 = complete destruction Table__________________________________________________________________________Active ingredient I + VII I + VIIIkg/ha 0.25+0.75 0.5+0.5 0.75+0.25 0.25+0.75 0.5+0.5 0.75+0.25__________________________________________________________________________Crop plantsTriticum aestivum 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0Gossypium hirsutum -- -- -- -- -- --Unwanted plantsAlopecurus myosuroides 86 94 92 100 100 93Stellaria media 80 66 55 73 64 54__________________________________________________________________________ The results of these experiments show that the mixtures have a herbicidal action far superior to the sum of the actions of their individual active ingredients.

Claims

1. A herbicide composition an inert carrier containing a herbicidally effective amount of a mixture consisting essentially of

a. N-propyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline and

b. a member selected from the group consisting of N-3,4-dichlorophenyl-N',N'-dimethylurea, N-3,4-dichlorophenyl-N'-methyl-N'-methoxyurea, N-(3-chloro-4-methylphenyl)-N',N'-dimethylurea, N-(3-trifluoromethylphenyl)-N',N'-dimethylurea, N-(3-chloro-4-methoxyphenyl)-N',N'-dimethylurea, and N-(3-chloro-4-methoxyphenyl)-N'-methyl-N'-methoxyurea in a weight ratio of a to b in the range of 3:1 to 1:3.

2. A herbicide composition as claimed in claim 1 wherein compound b is N-3,4-dichlorophenyl-N',N'-dimethylurea.

3. A herbicide composition as claimed in claim 1 wherein compound b is N-3,4-dichlorophenyl-N'-methyl-N'-methoxyurea.

4. A herbicide composition as claimed in claim 1 wherein compound b is N-(3-chloro-4-methylphenyl)-N',N'-dimethylurea.

5. A herbicide composition as claimed in claim 1 wherein compound b is N-(3-trifluoromethylphenyl)-N',N'-dimethylurea.

6. A herbicide composition as claimed in claim 1 wherein compound b is N-(3-chloro-4-methoxyphenyl)-N',N'-dimethylurea.

7. A herbicide composition as claimed in claim 1 wherein compound b is N-(3-chloro-4-methoxyphenyl)-N'-methyl-N'-methoxyurea.