Herbicide mixtures of 3-lower alkyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxides or salts thereof and 4-halobutynyl-N-halophenyl carbamates

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 or a salt thereof and (b) a compound of the formula ##EQU1## where R denotes halophenyl and R.sup.1 denotes haloalkynyl of 4 carbon atoms.

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.

It has been found that a composition of

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

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 ##EQU2## where denotes halophenyl and R.sup.1 denotes haloalkynyl of 4 carbon atoms, e.g. 4-chlorobutynyl, have a herbicidal action superior to that of their individual components.

Active ingredients a to b may be applied to 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 used 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 1

The plants wheat (Triticum aestivum), barley (Hordeum vulgare), wild oats (Avena fatua), slender foxtail (Alopecurus myosuroides), catchweed bedstraw (Galium aparine), chickweed (Stellaria media) and henbit (Lamium amplexicaule) were treated at a growth height of 4 to 20 cm with the following amounts of the following individual active ingredients and compositions thereof, each active ingredient and each composition being emulsified or dispersed in 500 liters of water per hectare:

I 4-chlorobutyn-2-yl-1 N-3-chlorophenylcarbamate, 1 and 2 kg per hectare; Ii 5-chloro-4-methyl-2-propionamide thiazole, 2 and 3 kg per hectare; Iii 3,5-dibromo-4-hydroxybenzaldoxime-O-(2',4'-dinitrophenyl)-ether, 0.75 and 1.5 kg per hectare; Iv 9-hydroxyfluorenecarboxylic acid-(9), 1 and 3 kg per hectare; V 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, 0.75, 1.5, 2 and 3 kg per hectare; I + v 1.0 + 1.0 kg per hectare; Ii + v 2.0 + 1.0 kg per hectare; Iii + v 0.75 + 0.75 kg per hectare; Iv + v 1.0 + 2.0 kg per hectare.

After 8 to 12 days it was acertained that the compositions had a better overall action than the individual active ingredients, combined with good crop plant compatibility. The results are given below:

__________________________________________________________________________Active ingredient I II III IV V I+V II+V III+V IV+Vkg/ha 1 2 2 3 0.75 1.5 1 3 0.75 1 1.5 2 3 1+1 2+1 0.75+0.75 1+2__________________________________________________________________________Triticum aestivum 0 0 10 20 0 10 0 0 0 0 0 0 0 0 10 0 0Hordeum vulgare 0 0 10 20 5 15 0 15 0 0 0 0 0 10 0 0Avena fatua 70 90 50 70 -- -- -- -- 5 5 5 .sup.[5 10 85 80 -- --Alopecurus 60 85 50 75 -- -- -- -- 5 5 10 10 15 80 80 -- --myosuroidesGalium aparine 5 10 30 45 20 45 30 85 35 40 60 70 80 80 90 90 100Stellaria media 10 30 40 65 30 70 30 90 40 60 70 90 90 90 100 100 100Lamium amplexicaule 5 10 5 10 45 80 30 95 30 40 50 60 70 75 75 100 100__________________________________________________________________________ 0 = no damage 100 = complete destruction

EXAMPLE 2

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

I 3-isopropyl-2,1,3-benzothiadiazinone-(4) -2,2-dioxide, 0.5, 0.75, 1 and 1.5 kg/ha; Ii 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt, 0.5, 0.75, 1 and 1.5 kg/ha; Iii 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt, 0.5, 0.75, 1 and 1.5 kg/ha; Iv 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt, 0.5, 0.75, 1 and 1.5 kg/ha; V 4-chlorobutyn-2-yl-1 N-3-chlorophenylcarbamate, 0.5, 0.75, 1 and 1.5 kg/ha; I+v, ii+v, iii+v and IV+V each of these compositions 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 good crop plant compatibility.

The results are given below:

Active I IIingredientkg/ha 0.5 0.75 1 1.5 0.5 0.75 1 1.5__________________________________________________________________________Cropplants:Triticum 0 0 0 0 0 0 0 0aestivumHordeum 0 0 0 0 0 0 0 0vulgareSecale 0 0 0 0 0 0 0 0cerealeUnwantedplants:Galium 30 35 40 60 30 40 45 60aparineAvena 0 2 5 5 0 0 0 5fatuaActive III IV Vingredientkg/ha 0.5 0.75 1 1.5 0.5 0.75 1 1.5 0.5 0.75 1 1.5__________________________________________________________________________Cropplants:Triticum 0 0 0 0 0 0 0 0 0 0 0 0aestivumHordeum 0 0 0 0 0 0 0 0 0 0 0 0vulgareSecale 0 0 0 0 0 0 0 0 0 0 0 0cerealeUnwantedplants:Galium 28 40 50 60 35 45 60 67 0 0 5 0aparineAvena 0 0 0 0 0 0 0 0 40 60 70 80fatua__________________________________________________________________________ 0 = no damage 100 = complete destruction __________________________________________________________________________Active ingredient I+V II+V III+V IV+Vkg/ha 0.5 1 0.75 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 1 0.5 0.75__________________________________________________________________________Crop 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:Gallium aparine 80 87 80 76 90 80 70 90 80 86 100 92Avena fatua 100 90 95 100 85 96 96 80 98 100 87 100__________________________________________________________________________ 0 = no damage 100 = complete destruction

EXAMPLE 3

In the greenhouse, various plants were treated at a growth height of from 1 to 25 cm with the following amounts of the following individual active ingredients and compositions thereof as dispersions, emulsions 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 4-chlorobutyn-2-yl-1 N-3-chlorophenylcarbamate each of these compounds at rates of 0.5, 1.5, 2, 2.5 and 3 kg/ha; I + v, ii + v, iii + v and IV + V, each at rates of 0.5 + 1.5, 1.5 + 0.5, 2.5 + 0.5 and 0.5 + 2.5 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 III IVkg/ha 0.5 1.5 2 2.5 3 0.5 1.5 2 2.5 3 0.5 1.5 2 2.5 3 0.5 1.5 2 2.5 3__________________________________________________________________________Crop plants:Triticum aestivum 0 0 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 0 0 0Secale cereale 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Unwanted plants:Galium aparine 30 60 75 90 95 30 60 80 90 94 28 60 75 90 95 35 67 80 90 95Avena fatua 0 5 7 9 10 0 5 7 10 10 0 0 3 6 10 0 0 2 10__________________________________________________________________________ 0 = no damage 100 = complete destruction __________________________________________________________________________Active ingredient V I + V II + V 0.5 1.5 2 2.5 3 1.5 0.5 2.5 0.5 1.5 0.5 2.5 0.5kg/ha 0.5 1.5 0.5 2.5 0.5 1.5 0.5 2.5__________________________________________________________________________Crop plants:Triticum oestivum 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 0Secale cereale 0 0 0 0 0 0 0 0 0 0 0 0 0Unwanted plants:Galium aparine 0 8 10 15 20 100 86 100 95 100 82 100 95Avena fatua 40 80 90 95 100 95 100 100 100 96 100 100 100__________________________________________________________________________ 0 = no damage 100 = complete destruction __________________________________________________________________________Active ingredient III + V IV + V 1.5 0.5 2.5 0.5 1.5 0.5 2.5 0.5kg/ha 0.5 1.5 0.5 2.5 0.5 1.5 0.5 2.5__________________________________________________________________________Crop plants:Triticum oestivum 0 0 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0 0 0Unwanted plants:Galium aparine 100 80 100 97 100 90 100 98Avena fatua 93 100 100 100 95 100 100 100__________________________________________________________________________ 0 = no damage 100 = complete destruction

Claims

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

a. a compound of the formula ##SPC2##

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

b. a compound of the formula ##EQU3## where R denotes chlorophenyl and R.sup.1 denotes 4-chlorobutynyl in a weight ratio of a:b of 5:1 to 1:5.

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

3. A composition as claimed in claim 1 wherein R in compound a is isopropyl, and compound b is 4-chlorobutyn-2-yl-1-N-3-chlorophenylcarbamate.

4. A herbicide composition as claimed in claim 3 wherein said weight ratio is 3:1 to 1:3.

5. A herbicide composition as claimed in claim 2 wherein said weight ratio is 3:1 to 1:3.

6. A herbicide composition as claimed in claim 1 wherein said weight ratio is 3:1 to 1:3.

7. A herbicide composition as claimed in claim 1 wherein compound a is 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide or the sodium, dimethylamine, or diethanolamine salt thereof.

8. A herbicide composition as claimed in claim 1 wherein compound a is 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide or the sodium, dimethylamine, or diethanolamine salt thereof, and compound b is 4-chlorobutyn-2-yl-1 N-3-chlorophenylcarbamate.