Herbicidal mixtures of 3-lower alkyl-2,1-3-benzothiadiazinone-(4)-2,2-dioxides or salts thereof and 1,1'-d'-dipyridylium salt

Abstract

Herbicide compositions of mixtures in the weight ratio of 5:1 to 1:5 of (a) 3-lower alkyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide and (b) a compound of the formula ##SPC1##Where R denotes the radical ##SPC2##And X denotes an anion (Cl.sup.-, Br.sup.-, methyl sulfate).

Description

The present invention relates to a herbicide comprising a composition of several active ingredients.

It is known that substituted phenyl ethers, carbamates, terephthalates, acid amides, benzoic acids, fluorenecarboxylic acids and benzothiadiazinones have a herbicidal action. However, this action is poor.

I have now found that a composition of

A. A COMPOUND OF THE FORMULA ##SPC3##

Where R denotes lower alkyl of a maximum of 4 carbon atoms, or its salts, such as alkali metal, alkaline earth metal, ammonium, hydroxyalkylammonium, alkylammonium and hydrazine salts, e.g. salts with sodium, lithium, potassium, calcium, iron, methylammonium, trimethylammonium, ethylammonium, diethanolammonium, ethanolammonium, dimethylamine, dimethylethanolamine, hydrazine and phenylhydrazine, and

B. A COMPOUND OF THE FORMULA ##SPC4##

Where R denotes the radical ##SPC5## And X denotes an anion (Cl.sup.- , Br.sup.- , methyl sulfate), have a herbicidal action superior to that of their individual components.

Active ingredients a to b may be applied in amounts of 0.5 to 5 kg per hectare.

The weight ratio of a : b is from 5:1 to 1:5, preferably from 3:1 to 1:3.

The compositions of the invention are suitable for controlling unwanted plants, e.g. dicotyledonous seed weeds, monocotyledonous grassy seed weeds and Cyperaceae in crops such as cereals, rice, soybeans, Indian corn, potatoes, peas, and beans.

The compositions may be applied to the loci of the plants, pre- and/or postemergence.

The agents according to the invention may be used as solutions, emulsions, suspensions oil dispersions, granules 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, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils and oils of vegetable or mineral origin, and cyclic hydrocarbons such as tetrahydronaphthalene and alkylated naphthalenes are suitable.

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, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent. Oils of various types may be added to ready-to-use spray liquors.

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

Granules may be prepared by bonding the active ingredients to solid carriers.

Directly sprayable dispersions may also be prepared with oils.

The new compounds may be mixed with fertilizers, insecticides, fungicides and other herbicides.

EXAMPLE I

In the greenhouse the plants and the soil are treated prior to the emergence of beet (Beta vulgaris) and potatoes (Solanum tuberosum) and after the emergence of wheat (Triticum aestivum) and the unwanted plants green foxtail (Setaria viridis), giant foxtail (Setaria faberii), barnyard grass (Echinochloa crus-galli), slender foxtail (Alopecurus myosuroides), silky bent grass (Apera spica venti), perennial ryegrass (Lolium perenne), bluegrass (Poa trivialis), catchweed bedstraw (Galium aparine), wild mustard (Sinapis arvensis), chamomile (Matricaria chamomilla) and common lambsquarters (Chenopodium album) are treated with the following amounts of the following individual active ingredients and compositions thereof:

I 1,1'-dimethyl-4,4'-dipyridylium-di-(methyl sulfate) 0.3 kg per hectare;II 1,1'-di-(3,5-dimethylmorpholinecarbonylmethyl)-4,4'-dipyridylium dichloride, 0.5 kg per hectare;III 1,1'-ethylene-2,2'-dipyridylium dibromide, 0.3 kg per hectare;IV 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, 0.5 kg per hectare;I + IV: 0.3 + 0.5 kg per hectare;II + IV: 0.5 + 0.5 kg per hectare;III + IV: 0.3 + 0.5 kg per hectare.

After 10 to 14 days it was ascertained that the compositions had a better herbicidal action than their individual components, combined with the same good crop plant compatibility.

The results are given below:

Active ingredient I II III IV I + IV II + IV III + IVkg/ha 0.3 0.5 0.3 0.5 0.3 + 0.5 0.5 + 0.5 0.3 + 0.5__________________________________________________________________________Beta vulgaris 10 0 0 0 0 0 0Solanum tuberosum 0 0 0 0 0 0 0Triticum aestivum -- 10 -- 0 -- 5 5Setaria viridis 40 25 30 5 90 80 85Setaria faberii 40 30 35 5 95 80 85Echinochloa crus-galli 35 25 30 0 85 75 80Alopecurus myosuroides 40 30 35 5 80 70 75Apera spica venti 50 40 45 10 100 90 95Lolium perenne 35 25 30 0 80 70 70Poa trivialis 40 30 35 5 85 75 80Calium aparine 35 30 30 35 90 80 80Matricaria chamomilla 40 35 35 35 95 80 85Sinapis arvensis 45 40 45 40 100 100 100Chenopodium album 45 40 40 45 100 100 100__________________________________________________________________________ 0 = no damage 100 = complete destruction

EXAMPLE 2

In the greenhouse, various plants were treated at a height of from 3 to 18 cm with the following amounts of the following individual active ingredients and compositions thereof as emulsions, dispersion, suspensions or aqueous solutions:

I 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide; Ii 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt; Iii 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt; Iv 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt; V 1,1-di-(3,5-dimethylmorpholinecarbonylmethyl)-4,4'-dipyridylium dichloride; Vi 1,1-di-(diethylcarbamoylmethyl)-4,4'-dipyridylium dichloride; each at rates of 0.5, 0.75, 1 and 1.5 kg/ha; I+V, II+V, III+V, IV+V, I+VI, II+VI, III+VI and IV+VI, each at rates of 0.5+1, 1+0.5 and 0.75+0.75 kg/ha. After 2 to 3 weeks it was ascertained that the compositions had a better herbicidal action than their components, combined with the same crop plant compatibility.

results are given below:

Active ingredient I II III IV Vkg/ha 0.5 0.75 1 1.5 0.5 0.75 1 1.5 0.5 0.75 1 1.5 0.5 0.75 1 1.5 0.5 0.75 1 1.5__________________________________________________________________________Crop plants:Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 10 15 20Hordeum vulgare 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 10 12 20Secale cereale 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 11 15 24Unwanted plants:Galium aparine 30 35 40 60 30 40 45 60 28 40 50 60 35 45 60 67 30 47 58 65Alopecurus myosuroides 2 5 5 10 3 8 12 15 5 7 10 16 4 7 12 15 30 35 42 50__________________________________________________________________________Active ingredient VI I + V II + V III + V IV + V I + VIkg/ha 0.5 1 0.75 0.5 1 0.75 0.5 1 0.75 0.5 1 0.75 0.5 1 0.75 0.5 0.75 1 1.5 1 0.5 0.75 1 0.5 0.75 1 0.5 0.75 1 0.5 0.75 1. 0.5 0.75__________________________________________________________________________Crop plants:Triticum aestivum 0 0 0 0 15 7 10 15 7 10 15 7 10 15 7 10 0 0 0Hordeum vulgare 0 0 0 0 12 5 10 12 5 10 12 5 10 12 5 10 0 0 0Secale cereale 0 0 0 0 15 7 11 15 7 11 15 7 11 15 7 11 0 0 0Unwanted plants:Galium aparine 20 25 34 40 100 100 100 100 100 100 100 100 100 100 100 100 100 98 97Alopecurusmyosuroides 40 45 50 60 90 80 85 87 80 85 94 80 86 90 82 86 95 90 94__________________________________________________________________________Active ingredient II+VI III+VI IV+VIkg/ha 0.5 1 0.75 0.5 1 0.75 0.5 1 0.75 1 0.5 0.75 1 0.5 0.75 1 0.5 0.75__________________________________________________________________________Crop plants:Triticum 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 0Unwanted plants:Galium aparine 100 100 100 97 100 100 100 100 100Alopecurus myosuroides 95 90 96 98 90 94 96 90 95__________________________________________________________________________ 0 = no damage 100 = complete destruction

EXAMPLE 3

In the greenhouse, various plants were treated at a height of from 3 to 18 cm with the following amounts of the following individual active ingredients and compositions thereof as emulsions, dispersions, suspensions or aqueous solutions:

I 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide; Ii 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt; Iii 3-isoproyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt; Iv 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt; V 1,1-di-(3,5-dimethylmorpholinecarbonylmethyl)-4,4'-dipyridylium dichloride; Vi 1,1-di-(diethylcarbamoylmethyl)-4,4'-dipyridylium dichloride; each at rates of 0.25, 0.5, 0.75, 1, 1.25 and 1.5 kg/ha; I+v, ii+v, iii+v, iv+v, i+vi, ii+vi, iii+vi and IV+VI, each at rates of 0.75+0.75, 0.25+1.25, 1.25+0.25, 0.25+0.75, 0.75+0.25 and 0.5+0.5 kg/ha. After 2 to 3 weeks it was ascertained that the compositions had a better herbicidal action than their components, combined with the same crop plant compatibility.

The results are given below:Active ingredient I II IIIkg/ha 0.25 0.5 0.75 1 1.25 1.5 0.25 0.5 0.75 1 1.25 1.5 0.25 0.5 0.75 1 1.25 1.5__________________________________________________________________________Crop plants:Triticum aestivum 0 0 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 0 0 0Secale cereale 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Unwanted plants:Galium aparine 20 30 35 40 55 60 15 30 40 45 55 60 20 28 40 50 55 60Alopecurus myosuroides 0 2 5 5 7 10 0 3 8 12 15 15 0 5 7 10 14 16__________________________________________________________________________ 0 = no damage? 100 = complete destruction?Active ingredient IV V VIkg/ha 0.25 0.5 0.75 1 1.25 1.5 0.25 0.5 0.75 1 1.25 1.5 0.25 0.5 0.75 1 1.25 1.5__________________________________________________________________________Crop plants:Triticum aestivum 0 0 0 0 0 0 5 7 10 15 18 20 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0 2 5 10 12 15 20 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0 3 7 11 15 20 24 0 0 0 0 0 0Unwanted plants:Galium aparine 25 35 45 60 65 67 15 30 47 58 60 65 10 20 25 35 38 40Alopecurusmyosuroides 0 4 7 12 15 15 10 30 35 42 48 50 30 40 45 50 55 60__________________________________________________________________________Active ingredient I+V II+Vkg/ha 0.75 0.25 1.25 0.25 0.75 0.5 0.75 0.25 1.25 0.25 0.75 0.5 0.75 1.25 0.25 0.75 0.25 0.5 0.75 1.25 0.25 0.75 0.25 0.5__________________________________________________________________________Crop plants:Triticum aestivum 10 18 5 10 5 7 10 18 5 10 5 7Hordeum vulgare 10 15 2 10 2 5 10 15 2 10 2 5Secale cereale 11 20 3 11 3 7 11 20 3 11 3 7Unwanted plants:Galium aparine 100 100 100 100 90 100 100 100 100 100 95 100Alopecurus myosuroides 85 90 60 75 60 72 85 90 65 75 60 75__________________________________________________________________________ III+V IV+V 0.75 0.25 1.25 0.75 1.25 0.25__________________________________________________________________________Crop plants:Triticum aestivum 10 18 5 10 5 7 10 18 5Hordeum vulgare 10 15 2 10 2 5 10 15 2Secale cereale 11 20 3 11 3 7 11 20 3Unwanted plants:Galium aparine 100 100 100 100 97 98 100 100 100Alopecurus myosuroides 86 90 65 75 60 75 86 96 70__________________________________________________________________________Active ingredient IV+V I+VI II+VIkg/ha 0.25 0.75 0.5 0.75 0.25 1.25 0.25 0.75 0.5 0.75 0.25 1.25 0.25 0.75 0.5 0.75 0.25 0.5 0.75 1.25 0.25 0.75 0.25 0.5 0.75 1.25 0.25 0.75 0.25 0.5__________________________________________________________________________Crop plants:Triticum aestivum 10 5 7 0 0 0 0 0 0 0 0 0 0 0 0Hordeum vulgare 10 2 5 0 0 0 0 0 0 0 0 0 0 0 0Secale cereale 11 3 7 0 0 0 0 0 0 0 0 0 0 0 0Unwanted plants:Galium aparine 100 100 100 100 100 100 85 87 90 100 95 100 80 90 90Alopecurus myosuroides 78 60 75 94 96 80 85 77 85 96 95 86 85 80 85__________________________________________________________________________ III+VI IV+VICrop plants:Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0 0 0 0 0 0 0Unwanted plants:Galium aparine 100 100 100 85 90 90 100 100 100 90 95 95Alopecurus myosuroides 94 96 85 85 80 87 95 96 85 87 80 85__________________________________________________________________________

Claims

1. A herbicide composition comprising an inert carrier having dispersed therein a herbicidally effective amount of a mixture consisting essentially of

a. a compound of the formula ##SPC6##

where R denotes lower alkyl of a maximum of 4 carbon atoms, or an alkali metal, alkaline earth metal, ammonium, lower hydroxyalkylammonium, lower alkylammonium or hydrazine salt thereof, and

b. a compound of the formula ##SPC7##

where R denotes the radical ##SPC8##

and X denotes an anion in a weight ratio of a:b of 3:1 to 1:3.

2. A herbicide composition as claimed in claim 1 wherein compound (b) is 1,1'-di-(3,5-dimethylmorpholinecarbonylmethyl)-4,4'-dipyridylium dichloride.

3. A herbicide composition as claimed in claim 1 wherein X is Cl.sup.- , Br.sup.- or methyl sulfate.

4. A process for controlling growth of unwanted plants among crop plants which comprises applying to the locus of the plants a herbicidally effective amount of a mixture of herbicides consisting essentially of

a. a compound of the formula ##SPC9##

where R denotes lower alkyl of a maximum of 4 carbon atoms, or an alkali metal, alkaline earth metal, ammonium, lower hydroxyalkylammonium, lower alkylammonium or hydrazine salt thereof, and

b. a compound of the formula ##SPC10##

where R denotes the radical ##SPC11##

and X denotes an anion in a weight ratio of a:b of 3:1 to 1:3.

5. A process as claimed in claim 4 wherein compound (b) is 1,1'-di-(3,5-dimethylmorpholinecarbonylmethyl)-4,4'-dipyridylium dichloride.

6. A process as claimed in claim 4 wherein X is Cl.sup.- , Br.sup.- or methyl sulfate.

7. A herbicide composition as claimed in claim 1 wherein R in compound a is isopropyl.

8. A herbicide composition as claimed in claim 1 wherein R in compound a is isopropyl, and said weight ratio is 1:1.

9. A process as claimed in claim 4 wherein R in compound a is isopropyl.

10. A process as claimed in claim 4 wherein R in compound a is isopropyl, and said weight ratio is 1:1.