Herbicide mixture of lower alkyl esters of N-benzoyl-N-chlorophenyl-2-amino-lower alkanoic acids and 3-lower alkyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxides or salts thereof

Information

  • Patent Grant
  • 3976468
  • Patent Number
    3,976,468
  • Date Filed
    Wednesday, July 10, 1974
    50 years ago
  • Date Issued
    Tuesday, August 24, 1976
    48 years ago
Abstract
New and valuable herbicides containing mixtures, inter alia, of lower alkyl esters of N-benzoyl-N-chlorophenyl-2-amino-lower alkanoic acids and 3-lower alkyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxides or salts thereof.
Description

The present invention relates to new and valuable herbicides containing compositions of different active ingredients.
It is known that benzoylaminocarboxylic acids, dinitrophenol derivatives, hydroxybenzonitriles, hydroxybenzaldoxime aryl ethers, benzothiadiazinone dioxides and phenoxycarboxylic acids have a herbicidal action. However, this action is not always satisfactory.
I have now found that a composition of
A. a compound of the formula ##EQU1## where X denotes halogen, alkyl, haloalkyl or alkoxy, R denotes hydrogen or lower alkyl, R.sup.1 denotes lower alkyl, and n denotes one of the integers 0, 1, 2 and 3, and/or
B. a compound of the formula ##EQU2## where R denotes lower alkyl, and R.sup.1 denotes hydrogen, or a salt thereof, e.g. ammonium, potassium, sodium, lithium, calcium, magnesium, ethylamine, dimethylamine, diethylamine, diethanolamine, ethanolamine, dimethylethanolamine, trimethylamine salts, and/or
C. a compound of the formula ##EQU3## where X denotes chloro, bromo, nitro, iodo, cyano or lower alkyl, n denotes one of the integers 0, 1, 2 and 3, and R denotes hydrogen and salts thereof, e.g. sodium and lithium salts, ##EQU4## Y denoting chloro, iodo or bromo, R.sup.1 denoting lower alkyl, ##EQU5## hydrogen and salts thereof, e.g., sodium salt, R.sup.2 denoting hydrogen, lower alkyl or a substituted or unsubstituted aryl radical, and R.sup.3 denoting hydrogen, lower alkyl or a substituted or unsubstituted aryl radical, and/or
D. a compound of the formula ##EQU6## where X denotes chloro or methyl, Y denotes chloro or methyl, n denotes one of the integers 0, 1, 2 and 3, R denotes hydrogen or lower alkyl, m denotes one of the integers 0, 1 and 2 and R.sup.1 denotes alkyl or hydrogen, or a salt thereof, e.g., sodium, potassium, dimethylamine, diethanolamine, and diethylamine salts, has a better herbicidal action than its constituents.
The compositions may contain one or more compounds of the formula a) and one of more compounds of the formulas b), c) or d).
The ratio of the active ingredients to each other is 1:0.1 to 10 parts by weight.
The amount used of the agents according to the invention may vary and depends in essence on the type of effect to be achieved; it is generally from 0.1 to 30 (and more), preferably 0.2 to 6, kg per hectare of active ingredient. The agents according to the invention may be used once or several times inter alia after planting, postemergence or during emergence of the crop or unwanted plants.
The compositions are selective in crops such as Triticum spp., Hordeum spp., Secale spp., Zea mays, Oryza sativa, Pisum sativum, Phaseolus vulgaris, Glycine max, and Solanum tuberosum.
The compositions may also be used as total herbicides on ditches, aquatic areas, railroad tracks, and barren or waste land, etc.
Compositions of a+b, a+c, a+d, a+b+c, a+b+d, a+c+d, and b+c+d are preferred.
Application may be effected for instance in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used; in any case they should ensure a fine distribution of the active ingredient.
For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coaltar oils, etc. and oil of vegetable or mineral origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc. are suitable.
Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.
Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts or dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.
Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silica gel, silicic acid, silica gels, silicates, talc, kaolin,, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.
The formulations contain 0.1 to 95, and preferably 0.5 to 90, % by weight of active ingredient.
There may be added to the compositions or individual active ingredients (if desired, immediately before use (tankmix) oils of various types, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, antifoams (e.g., silicones), growth regulators, antidotes and other herbicidally effective compounds such as substituted anilines substituted aryloxycarboxylic acids and salts, esters and amides thereof,
substituted ethers
substituted arsonic acids and their salts, esters and amides
substituted benzimidazoles
substituted benzisothiazoles
substituted benzothiadiazinone dioxides
substituted benzoxazines
substituted benzoxazinones
substituted benzothiadiazoles
substituted biurets
substituted quinolines
substituted carbamates
substituted aliphatic carboxylic acids and their salts, esters and amides
substituted aromatic carboxylic acids and their salts, esters and amides
substituted carbamoylalkylthiol- or -dithiophosphates
substituted quinazolines
substituted cycloalkylamidocarbothiolic acids and their salts, esters and amides
substituted cycloalkylcarbonamidothiazoles
substituted dicarboxylic acids and their salts, esters and amides
substituted dihydrobenzofuranyl sulfonates
substituted disulfides
substituted dipyridylium salts
substituted dithiocarbamates
substituted dithiophosphoric acids and their salts, esters and amides
substituted ureas
substituted hexahydro-1H-carbothioates
substituted hydantoins
substituted hydrazides
substituted hydrazonium salts
substituted isoxazole pyrimidones
substituted imidazoles
substituted isothiazole pyrimidones
substituted ketones
substituted naphthoquinones
substituted aliphatic nitriles
substituted aromatic nitriles
substituted oxadiazoles
substituted oxadiazinones
substituted oxadiazolidine diones
substituted oxadiazine diones
substituted phenols and their salts and esters
substituted phosphonic acids and their salts, esters and amides
substituted phosphonium chlorides
substituted phosphonalkyl glycines
substituted phosphites
substituted phosphoric acids and their salts, esters and amides
substituted piperidines
substituted pyrazoles
substituted pyrazole alkylcarboxylic acids and their salts, esters and amides
substituted pyrazolium salts
substituted pyrazolium alkyl sulfates
substituted pyridazines
substituted pyridine carboxylic acids and their salts, esters and amides
substituted pyridines
substituted pyridine carboxylates
substituted pyridinones
substituted pyrimidines
substituted pyrimidones
substituted pyrrolidine carboxylic acid and its salts, esters and amides
substituted pyrrolidines
substituted pyrrolidones
substituted arylsulfonic acids and their salts, esters and amides
substituted styrenes
substituted tetrahydrooxadiazine diones
substituted tetrahydroxadiazole diones
substituted tetrahydromethanoindenes
substituted tetrahydroxadiazole thiones
substituted tetrahydrothiadiazine thiones
substituted tetrahydrothiadiazole diones
substituted aromatic thiocarbonylamides
substituted thiocarboxylic acids and their salts, esters and amides
substituted thiol carbamates
substituted thioureas
substituted thiophosphoric acids and their salts, esters and amides
substituted triazines
substituted triazoles
substituted uracils, and
substituted uretidine diones.
The last-mentioned herbicidal compounds may also be applied before or after the active ingredients or compositions thereof according to the invention.
These agents may be added to the herbicides according to the invention in a ratio by weight of from 1:10 to 10:1. The same applies to oils, fungicides, nematocides, insecticides, bactericides, antidotes and growth regulators.
The new compositions have a strong herbicidal action and may therefore be used as weedkillers or for controlling the growth of unwanted plants. Whether the new active ingredients are used as total or selective agents depends in essence on the amount of ingredient used per unit area.
By weeds and unwanted plant growth are meant all monocotyledonous and dicotyledonous plants which grow in loci where they are not desired.
The agents according to the invention may therefore be used for controlling for instanceGramineae, such asCynodon spp. Dactylis spp.Digitaria spp. Avena spp.Echinochloa spp. Bromus spp.Setaria spp. Uniola spp.Panicum spp. Poa spp.Alopecurus spp. Leptochloa spp.Lolium spp. Brachiaria spp.Sorghum spp. Eleusine spp.Agropyron spp. Cenchrus spp.Phalaris spp. Eragrostis spp.Apera spp. Phragmitres communisetc.;Cyperaceae, such asCarex spp. Eleocharis spp.Cyperus spp. Scirpus spp.etc.;dicotyledonous weeds, such asMalvaceae, e.g.,Abutilon theoprasti Hibiscus spp.Sida spp. Malva spp.etc.;Compositae, such asAmbrosia spp. Centaurea spp.Lactuca spp. Tussilago spp.Senecio spp. Lapsana communisSonchus spp. Tagetes spp.Xanthium spp. Erigeron spp.Iva spp. Anthemis spp.Galinsoga spp. Matricaria spp.Taraxacum spp. Artemisia spp.Chrysanthemum spp. Bidens spp.Cirsium spp. etc.;Convolvulaceae, such asConvolvulus spp. Cuscuta spp.Ipomoea spp. Jaquemontia tamnifoliaetc.;Cruciferae, such asBarbarea vulgaris Arabidopsis thalianaBrassica spp. Descurainia spp.Capsella spp. Draba spp.Sisymbrium spp. Coronopus didymusThlaspi spp. Lepidium spp.Sinapis arvensis Raphanus spp.etc.;Geraniaceae, such asErodium spp. Geranium spp.etc.;Portulacaceae, such asPortulaca spp. etc.;Primulaceae, such isAnagallis arvensis Lysimachia spp.etc.;Rubiaceae, such asRichardia spp. Diodia spp.Galium spp. etc.;Scrophulariaceae, such asLinaria spp. Digitalis spp.Veronica spp. etc.;Solanaceae, such asPhysalis spp. Nicandra spp.Solanum spp. Datura spp.etc.;Urticaceae, such asUrtica spp.Violaceae, such asViola spp. etc.;Zygophyllaceae, such asTribulus terrestis etc.;Euphorbiaceae, such asMercurialis annua Euphorbia spp.Umbelliferae, such asDaucus carota Ammi majusAethusa cynapium etc.;Commelinaeae, such asCommelina spp. etc.;Labiatae, such asLamium spp. Galeopsis spp.etc.;Leguminosae, such asMedicago spp. Sesbania exaltataTrifolium spp. Cassia spp.Vicia spp. Lathyrus spp.etc.;Plantaginaceae, such asPlantago spp. etc.;Polygonaceae, such asPolygonum spp. Fagopyrum spp.Rumex spp. etc.;Aizoaceae, such asMollugo verticillata etc.;Amaranthaceae, such asAmaranthus spp. etc.;Boraginaceae, such asAmsinckia spp. Anchusa spp.Myostis spp. Lithospermum spp.etc.;Caryophyllaceae, such asStellaria spp. Silene spp.Spergula spp. Cerastium spp.Saponaria spp. Agrostemma githagoScleranthus annuus etc.;Chenopodiaceae, such asChenopodium spp. Atriplex spp.Kochia spp. Monolepsis nuttallianaSalsola Kali etc.;Lythraceae, such asCuphea spp. etc.;Oxalidaceae, such asOxalis spp.Ranunculaceae, such asRanunculus spp. Adonis spp.Delphinium spp. etc.;Papaveraceae, such asPapaver spp. Fumaria officinalisetc.;Onagraceae, such asJussiaea spp. etc.;Rosaceae, such asAlchemillia spp. Potentilla spp.etc.;Potamogetonaceae, such asPotamogeton spp. etc.;Najadaceae, such asNajas spp. etc.;EquisetaceaeEquisetum spp. etc.;Marsileaceae, such asMarsilea quadrifolia etc.;Polypodiaceae,Pteridium quilinumAlisamtaceaeAlisma spp. Sagittaria sagittifoliaetc.
In the greenhouse and in the open compositions of the following compounds were tested on the plants mentioned in the examples. The action of compositions of these compounds corresponds to that of the compositions in the examples:
3-methyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide
3-ethyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide
3-propyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide
3-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide
3-isobutyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt
3,5-dibromo-4-hydroxybenzaldoxime-O-(2',4'-dinitrophenyl)-ether
3,5-dibromo-4-hydroxybenzaldoxime-O-(2',4'-dinitrophenyl)-ether, sodium salt
3,5-dibromo-4-acetyloxybenzaldoxime-O-(2'-cyano-4'-nitrophenyl)-ether
3,5-dibromo-4-hydroxybenzaldoxime-O-(2'-cyano-4'-nitrophenyl)-ether
3,5-dibromo-4-hydroxybenzaldoxime-O-(2'-cyano-4'-cyanophenyl)-ether
3,5-dibromo-4-hydroxybenzaldoxime-O-(2'-cyano-4'-nitrophenyl)-ether, sodium salt
3,5-dibromo-4-propionyloxybenzaldoxime-O-(2'-cyano-4'-nitrophenyl)-ether
3,5-diiodo-4-hydroxybenzaldoxime-O-(2'-cyano-4'-nitrophenyl)-ether
3,5-diiodo-4-hydroxybenzaldoxime-O-(2'-cyano-4'-nitrophenyl)-ether, sodium salt
3,5-diiodo-4-hydroxybenzonitrile
3,5-diiodo-4-hydroxybenzonitrile, sodium salt
3,5-diiodo-4-hydroxybenzonitrile, lithium salt
3,5-dibromo-4-hydroxybenzonitrile
3,5-dibromo-4-hydroxybenzonitrile, sodium salt
3,5-dibromo-4-octanoyloxybenzonitrile
2-methyl-4,6-dinitrophenyl, sodium salt
2-sec-butyl-4,6-dinitrophenylacetate
2-tert-butyl-4,6-dinitrophenylacetate
2-tert-butyl-5-methyl-4,6-dinitrophenylacetate
2-isopropyl-3-methyl-4,6-dinitrophenol
2-sec-butyl-4,6-dinitrophenol, sodium salt
3,5-dibromo-4-phenylcarbamoyloxy-O-(2'-cyano-4'-nitrophenyl)-ether
3,5-dibromo-4-isopropylcarbamoyloxy-O-(2'-cyano-4'-nitrophenyl)-ether
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, methylamine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, trimethylamine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, ethylamine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethylamine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, ethanolamine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, aniline salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, pyridine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, phenylenediamine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, cyclohexylamine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dodecylhexamethylenimine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, hydrazine salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, magnesium salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, calcium salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, ammonium salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, potassium salt
3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, lithium salt
3-isobutyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt
3-isobutyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt
3-isobutyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt
3-sec-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt
3-sec-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt
3-sec-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt
3-n-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt
3-n-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt
3-n-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt
3-n-propyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt
3-n-propyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt
3-n-propyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt
3-ethyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt
3-ethyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt
3-ethyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt
3-methyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt
3-methyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt
3-methyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt
2-sec-amyl-4,6-dinitrophenol
2-(1-methylbutyl)-4,6-dinitrophenol
ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate
.alpha.-(2,4-dichlorophenoxy)-propionic acid, dimethylamine salt
.alpha.-(2-methyl-4-chlorophenoxy)-propionic acid, dimethylamine salt
.alpha.-(2-methyl-4-chlorophenoxy)-propionic acid, sodium salt
.alpha.-(2-methylphenoxy)-propionic acid, dimethylamine salt
.alpha.-(2,4-dichlorophenoxy)-propionic acid, sodium salt
.alpha.(2,4,5-trichlorophenoxy)-propionic acid, potassium salt
.alpha.-(4-chlorophenoxy)-propionic acid, dimethylamine salt
isooctyl .alpha.-(2-methylphenoxy)-propionate
.alpha.-(2-methylphenoxy)-proponic acid, sodium salt
.alpha.(2-methyl-4-chlorophenoxy)-propionic acid, diethanolamine salt
.alpha.-(2-methyl-4-chlorophenoxy)-propionic acid, potassium salt
isooctyl .alpha.-(2,4-dichlorophenoxy)-propionate
amyl 2,4,5-trichlorophenoxyacetate
isooctyl 2,4,5-trichlorophenoxyacetate
2,4,5-trichlorophenoxyacetic acid, diethylamine salt
2,4-dichlorophenoxyacetic acid, dimethylamine salt
2-methyl-4-chlorophenoxyacetic acid, dimethylamine salt
2-methyl-4-chlorophenoxyacetic acid, sodium salt
2,4,5-trichlorophenoxyacetic acid, potassium salt
2,4,5-trichlorophenoxyacetic acid, dimethylamine salt
4-chlorophenoxyacetic acid, dimethylamine salt
2-chlorophenoxyacetic acid, dimethylamine salt
isooctyl 2-methyl-4-chlorophenoxyacetate
2,4-dichlorophenoxyacetic acid, sodium salt
isooctyl 2,4-dichlorophenoxyacetate
.gamma.-(2,4-dichlorophenoxy)-butyric acid, dimethylamine salt
isooctyl .gamma.-(2,4-dichlorophenoxy)-butyrate
.gamma.-(2-methyl-4-chlorophenoxy)-butyric acid, sodium salt
.gamma.-(2,4,5-trichlorophenoxy)-butyric acid, dimethylamine salt
.gamma.-(4-chlorophenoxy)-butyric acid
.gamma.-(2,4-dichlorophenoxy)-crotonic acid, dimethylamine salt





EXAMPLE 1
In the greenhouse, various plants were treated at a growth height of from 2 to 18 cm with the following amounts of the following individual active ingredients and compositions thereof as emulsions or oil dispersions:
I. ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate, 0.5, 0.75, 1 and 1.5 kg/ha;
Ii. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, 0.5, 0.75, 1 and 1.5 kg/ha;
Iii. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt 0.5, 0.75, 1 and 1.5 kg/ha;
Iv. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt, 0.5, 0.75, 1 and 1.5 kg/ha;
V. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt, 0.5, 0.75, 1 and 1.5 kg/ha;
I+ii: 0.5+1, 1+0.5 and 0.75+0.75 kg/ha;
I+iii: 0.5+1, 1+0.5 and 0.75+0.75 kg/ha;
I+iv: 0.5+1, 1+0.5 and 0.75+0.75 kg/ha;
I+v: 0.5+1, 1+0.5 and 0.75+0.75 kg/ha.
After 14 to 18 days 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 give below:
__________________________________________________________________________Active ingredient I II IIIkg/ha 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 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:Avena fatua 25 37 45 60 0 0 0 0 0 0 0 0Galium aparine 0 6 10 14 35 45 60 75 30 40 60 75Stellaria media 7 10 12 15 30 40 60 70 20 30 55 70Active ingredient IV V__________________________________________________________________________Triticum aestivum 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 0Avena fatua 0 0 0 0 0 0 0 0Galium aparine 30 40 50 60 35 45 65 80Stellaria media 20 35 50 70 20 40 60 850 = no damage100 = complete destruction__________________________________________________________________________Active ingredient I+II I+IIIkg/ha 0.5+1 1+0.5 0.75+0.75 0.5+1 1+0.5 0.75+0.75__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0Avena fatua 67 90 75 65 87 73Galium aparine 95 92 90 97 80 85Stellaria media 100 80 93 96 75 80Active ingredient I+IV I+V__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0Avena fatua 70 92 78 68 90 80Galium aparine 94 85 90 97 87 95Stellaria media 98 78 86 100 80 900 = no damage100 = complete destruction__________________________________________________________________________
EXAMPLE 2
In the greenhouse, various plants were treated at a growth height of from 3 to 25 cm with the following amounts of the following individual active ingredients and compositions thereof as dispersions:
I. ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate, 0.5, 1.5, 2.5 and 3 kg/ha;
Ii. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, 0.5, 1.5, 2.5 and 3 kg/ha;
Iii. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt, 0.5, 1.5, 2.5 and 3 kg/ha;
Iv. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt, 0.5, 1.5, 2.5 and 3 kg/ha;
V. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt, 0.5, 1.5, 2.5 and 3 kg/ha;
I+ii: 2.5+0.5, 0.5+2.5 and 1.5+1.5 kg/ha;
I+iii: 2.5+0.5, 0.5+2.5 and 1.5+1.5 kg/ha;
I+iv 2.5+0.5, 0.5+2.5 and 1.5+1.5 kg/ha;
I+v: 2.5+0.5, 0.5+2.5 and 1.5+1.5 kg/ha;
After 15 to 18 days 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 ingredient I II IIIkg/ha 0.5 1.5 2.5 3 0.5 1.5 2.5 3 0.5 1.5 2.5 3__________________________________________________________________________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:Avena fatua 25 60 78 95 0 0 0 0 0 0 0 0Galium aparine 0 14 23 35 35 75 90 95 30 75 90 95Stellaria media 7 15 20 29 30 70 86 95 20 70 90 94Active ingredient IV V__________________________________________________________________________Triticum aestivum 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 0Avena fatua 0 0 0 0 0 0 0 0Galium aparine 30 60 90 100 35 80 90 95Stellaria media 20 70 93 95 20 85 100 1000 = no damage100 = complete destruction__________________________________________________________________________ I+II I+III I+IV I+VActive ingredient 2.5+ 1.5+ 0.5+ 2.5+ 1.5+ 0.5+ 2.5+ 1.5+ 0.5+ 2.5+ 1.5+ 0.5+kg/ha 0.5 1.5 2.5 0.5 1.5 2.5 0.5 1.5 2.5 0.5 1.5 2.5__________________________________________________________________________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 0Avena fatua 100 96 70 100 95 72 100 97 70 100 95 68Galium aparine 97 100 100 98 100 100 96 100 100 100 100 100Stellaria media 96 100 100 90 100 100 87 100 100 90 100 1000 = no damage100 = complete destruction__________________________________________________________________________
EXAMPLE 3
In the greenhouse, various plants were treated at a growth height of from 2 to 20 cm with the following amounts of the following individual active ingredients and compositions thereof as pastes:
I. ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate, 0.25, 1 and 1.5 kg/ha;
Iv. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt, 0.25, 1 and 1.5 kg/ha;
Vi. 2-sec-butyl-4,6-dinitrophenyl acetate, 0.25, 1 and 1.5 kg/ha;
Vii. 3,5-diiodo-4-hydroxybenzonitrile, lithium salt, 0.25, 1 and 1.5 kg/ha;
Viii. 3,5-dibromo-4-hydroxybenzaldoxime-O-(2',4'-dinitrophenyl)-ether, sodium salt, 0.25, 1 and 1.5 kg/ha;
Ix. 3,5-dibromo-4-hydroxybenzaldoxime-O-(2'-cyano-4'-nitrophenyl)-ether, sodium salt, 0.25, 1 and 1.5 kg/ha;
I+iv+vii; 1+0.25+0.25, 0.25+1+0.25 and 0.25+0.25+1 kg/ha;
I+iv+viii: 1+0.25+0.25, 0.25+1+0.25 and 0.25+0.25+1 kg/ha;
I+iv+ix: 1+0.25+0.25, 0.25+1+0.25 and 0.25+0.25+1 kg/ha;
I+iv+vi: 1+0.25+0.25, 0.25+1+0.25 and 0.25+0.25+1 kg/ha.
After 12 to 14 days 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 ingredient I IV VI VIIkg/ha 0.25 1 1.5 0.25 1 1.5 0.25 1 1.5 0.25 1 1.5__________________________________________________________________________Crop plants:Triticum aestivum 0 0 0 0 0 0 0 0 0 0 10 20Hordeum vulgare 0 0 0 0 0 0 0 0 0 0 10 10Secale cereale 0 0 0 0 0 0 0 0 0 0 20 20Unwanted plants:Avena fatua 10 45 60 0 0 0 0 10 15 0 0 0Galium aparine 0 10 14 20 50 60 18 40 50 15 60 70Stellaria media 5 12 15 25 50 75 20 60 75 25 55 80Active ingredient VIII IX__________________________________________________________________________Triticum aestivum 0 0 10 0 0 0Hordeum vulgare 0 0 15 0 0 0Secale cereale 0 0 15 0 0 5Avena fatua 0 0 0 0 0 0Galium aparine 20 50 60 25 95 100Stellaria media 15 48 70 20 80 1000 = no damage100 = complete destruction__________________________________________________________________________Active ingredient I+IV+VI I+IV+VIIkg/ha 1+0.25+0.25 0.25+1+0.25 0.25+0.25+1 1+0.25+0.25 0.25+1+0.25 0.25+0.25+1__________________________________________________________________________Triticum aestivum 0 0 0 0 0 10Hordeum vulgare 0 0 0 0 0 10Secale cereale 0 0 0 0 0 20Avena fatua 87 58 60 80 54 57Galium aparine 90 95 90 87 97 90Stellaria media 95 92 100 98 100 100Active ingredient I+IV+VIII I+IV+IX__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0Avena fatua 90 62 65 92 60 64Galium aparine 93 100 100 98 100 100Stellaria media 95 100 100 100 100 1000 = no damage100 = complete destruction__________________________________________________________________________
EXAMPLE 4
In the open, various plants were treated at a growth height of from 2 to 24 cm with the following amounts of the following individual active ingredients and compositions thereof as tankmix emulsions or dispersions:
I. ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate, 0.25, 1 and 1.5 kg/ha;
Ii. 3-isopropyl-2,1,3-benzothiadiazinon-(4)-2,2-dioxide, 0.25, 1 and 1.5 kg/ha;
Iii. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt, 0.25, 1 and 1.5 kg/ha;
Iv. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt, 0.25, 1 and 1.5 kg/ha;
V. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt, 0.25, 1 and 1.5 kg/ha;
Vi. 2-sec-butyl-4,6-dinitrophenyl acetate, 0.25, 1 and 1.5 kg/ha;
Vii. 3,5-diiodo-4-hydroxybenzonitrile, lithium salt, 0.25, 1 and 1.5 kg/ha;
Viii. 3,5-dibromo-4-hydroxybenzaldoxime-O-(2',4'-dinitrophenyl)-ether, sodium salt, 0.25, 1 and 1.5 kg/ha;
Ix. 3,5-dibromo-4-hydroxybenzaldoxime-O-(2'-cyano-4'-nitrophenyl)-ether, sodium salt, 0.25, 1 and 1.5 kg/ha;
X. 3,5-dibromo-4-hydroxybenzonitrile, sodium salt, 0.25, 1 and 1.5 kg/ha;
Xi. .alpha.-(2-methyl-4-chlorophenoxy)-propionic acid, dimethylamine salt, 0.25, 1 and 1.5 kg/ha;
Xii. .alpha.-(2,4-dichlorophenoxy)-propionic acid, dimethylamine salt, 0.25, 1 and 1.5 kg/ha;
Xiii. 2,4-dichlorophenoxyacetic acid, dimethylamine salt, 0.25, 1 and 1.5 kg/ha;
Xiv. 2-methyl-4-chlorophenoxyacetic acid, dimethylamine salt, 0.25, 1 and 1.5 kg/ha;
Xv. .alpha.-(2,4,5-trichlorophenoxy)-propionic acid, dimethylamine salt, 0.25, 1 and 1.5 kg/ha;
Xvi. 2,4,5-trichlorophenoxyacetic acid, potassium salt, 0.25, 1 and 1.5 kg/ha;
Xvii. .gamma.-(2,4-dichlorophenoxy)-butyric acid, dimethylamine salt, 0.25, 1 and 1.5 kg/ha;
I+ii+vi, i+ii+vii, i+ii+viii, i+ii+ix, i+ii+x, i+iii+vi, i+iii+vii,
i+iii+viii, i+iii+ix, i+iii+x, i+v+vi, i+v+vii, i+v+viii, i+v+ix,
i+v+x, i+iv+x, i+ii+ix, i+ii+xii, i+ii+xiii, i+ii+xiv, i+ii+xv,
i+ii+xvi, i+iii+xi, i+iii+xii, i+iii+xiii, i+iii+xiv, i+iii+xv,
i+iii+xvi, i+iv+xi, i+iv+xii, i+iv+xiii, i+iv+xiv, i+iv+xv, i+iv+xvi,
i+v+xi, i+v+xii, i+v+xiii, i+v+xiv, i+v+xv, i+v+xvi, i+vi+xi,
i+vi+xii, i+vi+xiii, i+vi+xiv, i+vi+xv, i+vi+xvi, i+vii+xi, i+vii+xii,
i+vii+xiii, i+vii+xiv, i+vii+xv, i+vii+xvi, i+viii+xi, i+viii+xii,
i+viii+xiii, i+viii+xiv, i+viii+xv, i+viii+xvi, i+ix+xi, i+ix+xii,
i+ix+xiii, i+ix+xiv, i+ix+xv, i+ix+xvi, i+x+xi, i+x+xii, i+x+xiii,
i+x+xiv, i+x+xv, i+x+xvi, i+xvi+xi, i+xvi+xii, i+xvi+xiii, i+xvi+xiv,
i+xiii+xi, i+xiii+xiv, i+ii+xvii, i+iii+xvii, i+iv+xii, i+v+xvii,
i+vi+xvii, i+vii+xvii, i+viii+xvii, i+ix+xvii, i+x+xvii, each of the above compositions at rates of 1+0.25+0.25, 0.25+1+0.25 and 0.25+0.25+1 kg/ha.
After 12 to 14 days 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 ingredient I II III IVkg/ha 0.25 1 1.5 0.25 1 1.5 0.25 1 1.5 0.25 1 1.5__________________________________________________________________________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:Avena fatua 10 45 60 0 0 0 0 0 0 0 0 0Galium aparine 0 10 14 15 60 75 15 60 75 20 50 60Stellaria media 5 12 15 25 60 70 10 55 70 25 50 70Active ingredient V VI VII VIII__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 10 20 0 0 10Hordeum vulgare 0 0 0 0 0 0 0 10 10 0 0 15Secale cereale 0 0 0 0 0 5 0 20 20 0 0 10Avena fatua 0 0 0 0 10 15 0 0 0 0 0 0Galium aparine 25 65 80 18 40 50 15 60 70 20 50 60Stellaria media 10 60 85 20 60 75 25 55 80 15 48 70Active ingredient IX X XI XII__________________________________________________________________________Triticum aestivum 0 0 0 0 10 12 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 5 6 0 0 0 0 0 0Secale cereale 0 0 5 0 8 10 0 0 0 0 0 0Avena fatua 0 0 0 0 0 0 0 0 0 0 0 5Galium aparine 25 90 100 10 50 67 15 50 70 10 65 75Stellaria media 20 80 100 15 54 78 20 45 70 15 55 75Active ingredient XIII XIV XV XVI__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 5 10 0 0 0Hordeum vulgare 0 0 0 0 0 0 0 7 10 0 0 5Secale cereale 0 0 0 0 0 0 0 10 12 0 0 7Avena fatua 0 0 0 0 0 0 0 4 10 0 0 0Galium aparine 5 20 25 5 20 25 20 60 85 15 60 80Stellaria media 3 10 20 10 20 35 15 65 85 5 20 36Active ingredient XVII__________________________________________________________________________Triticum aestivum 0 0 0Hordeum vulgare 0 0 0Secale cereale 0 0 0Avena fatua 0 0 0Galium aparine 9 18 25Stellaria media 2 8 15Active ingredient I+II+VI I+II+VII I+II+VIII 1+ 0.25+ 0.25+ 1+ 0.25+ 0.25+ 1+ 0.25+ 0.25+kg/ha 0.25+ 1+ 0.25+ 0.25+ 1+ 0.25+ 0.25+ 1+ 0.25+ 0.25 0.25 1 0.25 0.25 1 0.25 0.25 1__________________________________________________________________________Triticum aestivum 0 0 0 0 0 10 0 0 0Hordeum vulgare 0 0 0 0 0 10 0 0 0Secale cereale 0 0 0 0 0 20 0 0 0Avena fatua 90 56 65 80 50 52 77 48 50Galium aparine 85 100 98 84 100 100 90 100 100Stellaria media 90 100 100 100 100 100 96 100 100Active ingredient I+II+IX I+II+X I+III+VI__________________________________________________________________________Triticum aestivum 0 0 0 0 0 10 0 0 0Hordeum vulgare 0 0 0 0 0 5 0 0 0Secale cereale 0 0 0 0 0 8 0 0 0Avena fatua 80 52 54 75 49 50 90 55 64Galium aparine 87 100 100 78 98 100 75 100 93Stellaria media 100 100 100 90 100 100 80 100 97Active ingredient I+III+VII I+III+VIII I+III+IX__________________________________________________________________________Triticum aestivum 0 0 10 0 0 0 0 0 0Hordeum vulgare 0 0 10 0 0 0 0 0 0Secale cereale 0 0 20 0 0 0 0 0 0Avena fatua 82 50 53 82 54 57 80 52 54Galium aparine 80 100 100 84 100 98 85 100 100Stellaria media 98 100 100 75 100 95 80 100 100Active ingredient I+III+X I+V+VI I+V+VII__________________________________________________________________________Triticum aestivum 0 0 10 0 0 0 0 0 10Hordeum vulgare 0 0 5 0 0 0 0 0 10Secale cereale 0 0 8 0 0 0 0 0 20Avena fatua 76 48 50 83 53 66 80 48 50Galium aparine 74 100 98 92 100 97 90 100 100Stellaria media 80 100 100 85 100 100 88 100 97Active ingredient I+V+VIII I+V+IX I+V+X__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 0 10Hordeum vulgare 0 0 0 0 0 0 0 0 5Secale cereale 0 0 0 0 0 0 0 0 8Avena fatua 90 55 60 88 53 58 80 47 48Galium aparine 92 100 100 100 100 100 87 100 100Stellaria media 82 100 98 86 100 100 83 100 98Active ingredient I+IV+X I+II+XI I+II+XII__________________________________________________________________________Triticum aestivum 0 0 10 0 0 0 0 0 0Hordeum vulgare 0 0 5 0 0 0 0 0 0Secale cereale 0 0 8 0 0 0 0 0 0Avena fatua 82 50 50 83 49 48 86 52 56Galium aparine 80 95 100 84 100 94 76 100 100Stellaria media 90 100 100 100 100 100 90 100 100Active ingredient I+II+XIII I+II+XIV I+II+XV__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 0 5Hordeum vulgare 0 0 0 0 0 0 0 0 7Secale cereale 0 0 0 0 0 0 0 0 10Avena fatua 82 48 47 80 49 50 85 53 55Galium aparine 73 93 77 72 98 75 96 100 100Stellaria media 80 96 82 90 100 88 90 100 100Active ingredient I+II+XVI I+III+XI I+III+XII__________________________________________________________________________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 0Avena fatua 80 47 49 82 49 51 86 52 54Galium aparine 88 100 100 83 100 94 77 100 100Stellaria media 80 100 88 80 100 96 80 100 100Active ingredient I+III+XIII I+III+XIV I+III+XV__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 0 5Hordeum vulgare 0 0 0 0 0 0 0 0 7Secale cereale 0 0 0 0 0 0 0 0 10Avena fatua 81 50 49 83 50 49 84 52 54Galium aparine 73 97 75 74 95 77 90 100 100Stellaria media 68 96 70 75 100 76 82 100 100Active ingredient I+III+XVI I+IV+XI I+IV+XII__________________________________________________________________________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 0Avena fatua 80 47 49 87 50 55 92 56 55Galium aparine 83 100 100 90 96 100 78 97 100Stellaria media 70 95 76 94 100 100 90 100 100Active ingredient I+IV+ XIII I+IV+XIV I+IV+XV__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 0 5Hordeum vulgare 0 0 0 0 0 0 0 0 7Secale cereale 0 0 0 0 0 0 0 0 10Avena fatua 78 48 47 80 47 49 85 50 60Galium aparine 75 90 75 72 92 80 87 100 100Stellaria media 78 100 82 85 97 93 90 100 100Active ingredient I+IV+XVI I+V+XI I+V+XII__________________________________________________________________________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 0Avena fatua 80 47 49 83 52 50 85 60 60Galium aparine 84 100 100 86 100 100 85 100 100Stellaria media 80 98 87 84 100 97 86 100 100Active ingredient I+V+XIII I+ V+XIV I+V+XV__________________________________________________________________________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 0Avena fatua 85 50 48 85 52 50 85 54 52Galium aparine 83 100 85 82 100 85 95 100 100Stellaria media 75 100 70 80 100 80 85 100 100Active ingredient I+V+XVI I+VI+XI I+VI+XII__________________________________________________________________________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 0Avena fatua 85 50 48 85 52 54 85 55 56Galium aparine 90 100 100 83 95 100 78 90 100Stellaria media 76 100 82 92 100 100 87 100 100Active ingredient I+VI+XIII I+VI+XIV I+VI+XV__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 0 5Hordeum vulgare 0 0 0 0 0 0 0 0 7Secale cereale 0 0 0 0 0 0 0 0 10Avena fatua 82 68 46 80 60 49 85 60 56Galium aparine 70 80 77 70 83 50 88 100 100Stellaria media 78 98 76 80 100 85 87 100 100Active ingredient I+VI+XVI I+VII+XI I+VII+XII__________________________________________________________________________Triticum aestivum 0 0 0 0 10 0 0 10 0Hordeum vulgare 0 0 0 0 10 0 0 10 0Secale cereale 0 0 0 0 20 0 0 20 0Avena fatua 85 59 48 86 50 50 85 51 50Galium aparine 83 95 100 80 100 100 75 100 100Stellaria media 77 100 85 97 100 100 92 100 100Active ingredient I+VII+XIII I+VII+XIV I+VII+ XV__________________________________________________________________________Triticum aestivum 0 10 0 0 10 0 0 10 5Hordeum vulgare 0 10 0 0 10 0 0 10 7Secale cereale 0 20 0 0 20 0 0 20 10Avena fatua 86 50 49 85 50 49 86 51 54Galium aparine 72 100 75 72 100 75 87 100 100Stellaria media 83 100 82 87 100 90 92 100 100Active ingredient I+VII+XVI I+VIII+XI I+VIII+XII__________________________________________________________________________Triticum aestivum 0 10 0 0 0 0 0 0 0Hordeum vulgare 0 10 0 0 0 0 0 0 0Secale cereale 0 20 0 0 0 0 0 0 0Avena fatua 85 52 50 85 48 49 84 50 49Galium aparine 82 100 100 85 100 100 80 100 100Stellaria media 83 100 90 87 100 100 82 100 100Active ingredient I+VIII+XIII I+VIII+XIV I+VIII+XV__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 0 5Hordeum vulgare 0 0 0 0 0 0 0 0 7Secale cereale 0 0 0 0 0 0 0 0 10Avena fatua 85 50 51 86 49 51 85 50 54Galium aparine 75 95 80 75 95 80 90 100 100Stellaria media 72 96 71 77 100 75 82 100 100Active ingredient I+VIII+XVI I+IX+XI I+IX+XII__________________________________________________________________________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 0Avena fatua 83 50 52 85 51 50 84 51 50Galium aparine 85 100 100 90 100 100 92 100 100Stellaria media 72 98 82 92 100 100 96 100 100Active ingredient I+IX+XIII I+IX+XIV I+IX+XV__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 0 5Hordeum vulgare 0 0 0 0 0 0 0 0 7Secale cereale 0 0 0 0 0 0 0 0 10Avena fatua 86 49 50 84 48 49 84 50 54Galium aparine 80 100 90 80 100 87 100 100 100Stellaria media 80 100 80 85 100 86 100 100 100Active ingredient I+IX+XVI I+X+XI I+X+XII__________________________________________________________________________Triticum aestivum 0 0 0 0 10 0 0 10 0Hordeum vulgare 0 0 0 0 5 0 0 5 0Secale cereale 0 0 0 0 8 0 0 8 0Avena fatua 80 50 52 78 53 55 85 56 54Galium aparine 95 100 100 75 100 100 76 94 98Stellaria media 80 100 86 87 100 100 80 100 100Active ingredient I+X+XIII I+X+XIV I+X+XV__________________________________________________________________________Triticum aestivum 0 10 0 0 10 0 0 10 5Hordeum vulgare 0 5 0 0 5 0 0 7 7Secale cereale 0 8 0 0 8 0 0 10 10Avena fatua 82 50 48 78 52 50 84 54 60Galium aparine 70 90 68 65 93 77 83 100 100Stellaria media 75 90 76 80 100 82 85 100 100Active ingredient I+X+XVI I+XVI+XI I+XVI+XII__________________________________________________________________________Triticum aestivum 0 10 0 0 0 0 0 0 0Hordeum vulgare 0 5 0 0 0 0 0 0 0Secale cereale 0 8 0 0 0 0 0 0 0Avena fatua 80 49 48 83 54 60 88 52 60Galium aparine 78 94 100 80 100 100 82 100 100Stellaria media 76 98 80 75 97 100 75 80 100Active ingredient I+XVI+ XIII I+XVI+XIV I+XIII+XI__________________________________________________________________________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 0Avena fatua 77 48 47 76 50 48 85 47 52Galium aparine 74 100 75 74 97 76 78 70 98Stellaria media 65 75 63 70 75 70 80 74 95Active ingredient I+XIII+XIV I+II+XVII I+III+XVII__________________________________________________________________________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 0Avena fatua 78 50 48 80 47 50 79 50 48Galium aparine 64 80 66 75 100 74 75 100 76Stellaria media 68 75 69 80 100 75 68 98 68Active ingredient I+IV+XVII I+V+XVII I+VI+XVII__________________________________________________________________________Triticum aestivum 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 0Avena fatua 80 52 49 80 51 50 85 68 55Galium aparine 80 100 80 82 100 80 78 90 72Stellaria media 75 100 77 70 100 70 75 100 74Active ingredient I+VII+XVII I+VIII+XVII I+IX+XVII__________________________________________________________________________Triticum aestivum 0 10 0 0 0 0 0 0 0Hordeum vulgare 0 10 0 0 0 0 0 0 0Secale cereale 0 20 0 0 0 0 0 0 0Avena fatua 76 50 48 78 47 51 80 50 48Galium aparine 72 100 70 77 98 76 87 100 90Stellaria media 80 100 79 70 95 70 80 100 82Active ingredient I+X+XVII__________________________________________________________________________Triticum aestivum 0 10 0Hordeum vulgare 0 5 0Secale cereale 0 8 0Avena fatua 78 52 50Galium aparine 65 100 70Stellaria media 74 100 72__________________________________________________________________________ 0 = no damage 100 = complete destruction
EXAMPLE 5
In the greenhouse, various plants were treated at a growth height of from 2 to 24 cm with the following amounts of the following individual active ingredients and compositions thereof as tankmix emulsions or solutions:
I. ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate, 0.5 and 1.5 kg/ha;
Ii. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, 0.5 and 1.5 kg/ha;
Iii. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt, 0.5 and 1.5 kg/ha;
Iv. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt, 0.5 and 1.5 kg/ha;
V. 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt, 0.5 and 1.5 kg/ha;
Xi. .alpha.-(2-methyl-4-chlorophenoxy)-propionic acid, dimethylamine salt, 0.25 and 1.5 kg/ha;
Xii. .alpha.-(2,4-dichlorophenoxy)-propionic acid, dimethylamine salt, 0.25 and 1.5 kg/ha;
Xiii. 2,4-dichlorophenoxyacetic acid, dimethylamine salt, 0.25 and 1.5 kg/ha;
Xiv. 2-methyl-4-chlorophenoxyacetic acid, dimethylamine salt, 0.25 and 1.5 kg/ha;
Xv. .alpha.-(2,4,5-trichlorophenoxy)-propionic acid, dimethylamine salt, 0.25 and 1.5 kg/ha;
Xvi. 2,4,5-trichlorophenoxyacetic acid, potassium salt, 0.25 and 1.5 kg/ha;
Xvii. .gamma.-(2,4-dichlorophenoxy)-butyric acid, dimethylamine salt, 0.25 and 1.5 kg/ha;
I+ii+xii+xvi i+iii+xii+xvi i+iv+xii+xvi i+v+xii+xvi i+ii+xiv+xvi
i+iii+xiv+xvi i+iv+xiv+xvi i+v+xiv+xvi i+ii+xiii+xvi
i+iii+xiii+xvi i+iv+xiii+xvi i+v+xiii+xvi i+ii+xi+xvi i+iii+xi+xvi
i+iv+xi+xvi i+v+xi+xvi i+ii+xiii+xi i+iii+xiii+xi i+iv+xiii+xi
i+v+xiii+xi i+ii+xiii+xiv i+iii+xiii+xiv i+iv+xiii+xiv i+v+xiii+xiv each of these compositions at a rate of 0.5+0.25+0.25+0.25 kg/ha. After 12 to 15 days 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 ingredient I II III IV Vkg/ha 0.5 1.5 0.5 1.5 0.5 1.5 0.5 1.5 0.5 1.5__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0 0 0 0 0Secale cereale 0 0 0 0 0 0 0 0 0 0Avena fatua 26 60 0 0 0 0 0 0 0 0Galium aparine 0 14 35 75 30 75 30 60 35 80Stellaria media 7 15 30 70 20 70 20 70 20 85Active ingredient XI XII XIII XIV XVI__________________________________________________________________________Triticum aestivum 0 0 0 0 0 0 0 0 0 0Hordeum vulgare 0 0 0 0 0 0 0 0 0 5Secale cereale 0 0 0 0 0 0 0 0 0 7Avena fatua 0 0 0 5 0 0 0 0 0 0Galium aparine 15 70 10 75 5 25 5 25 15 80Stellaria media 20 70 15 75 3 20 10 35 5 36Active ingredient I+II+XII+XVI I+III+XII+XVI I+IV+XII+XVIkg/ha 0.5+0.5+0.25+0.25 0.5+0.5+0.25+0.25 0.5+0.5+0.25+0.25__________________________________________________________________________Triticum aestivum 0 0 0Hordeum vulgare 0 0 0Secale cereale 0 0 0Avena fatua 74 72 70Galium aparine 100 100 100Stellaria media 100 93 94Active ingredient I+V+XII+XVI I+II+XIV+XVI I+III+XIV+XVI__________________________________________________________________________Triticum aestivum 0 0 0Hordeum vulgare 0 0 0Secale cereale 0 0 0Avena fatua 69 64 65 Galium aparine 100 90 90Stellaria media 93 88 80Active ingredient I+IV+XIV+XVI I+V+XIV+XVI I+II+XIII+XVI__________________________________________________________________________Triticum aestivum 0 0 0Hordeum vulgare 0 0 0Secale cereale 0 0 0Avena fatua 62 60 60Galium aparine 89 92 90Stellaria media 78 80 80Active ingredient I+III+XIII+XVI I+IV+XIII+XVI I+V+XIII+XVI__________________________________________________________________________Triticum aestivum 0 0 0Hordeum vulgare 0 0 0Secale cereale 0 0 0Avena fatua 62 65 64Galium aparine 87 90 92Stellaria media 77 80 79Active ingredient I+II+XI+XVI I+III+XI+XVI I+IV+XI+XVI__________________________________________________________________________Triticum aestivum 0 0 0Hordeum vulgare 0 0 0Secale cereale 0 0 0Avena fatua 70 69 68Galium aparine 100 100 100Stellaria media 98 96 95Active ingredient I+V+XI+XVI I+II+XIII+XI I+III+XIII+XI__________________________________________________________________________Triticum aestivum 0 0 0Hordeum vulgare 0 0 0Secale cereale 0 0 0Avena fatua 68 66 65Galium aparine 100 95 90Stellaria media 93 98 94Active ingredient I+IV+XIII+XI I+V+XIII+XI I+II+XIII+ XIV__________________________________________________________________________Triticum aestivum 0 0 0Hordeum vulgare 0 0 0Secale cereale 0 0 0Avena fatua 64 65 62Galium aparine 92 97 82Stellaria media 90 95 87Active ingredient I+III+XIII+XIV I+IV+XIII+XIV I+V+XIII+XIV__________________________________________________________________________Triticum aestivum 0 0 0Hordeum vulgare 0 0 0Secale cereale 0 0 0Avena fatua 60 60 63Galium aparine 78 80 83Stellaria media 80 77 84__________________________________________________________________________ 0 = no damage 100 = complete destruction
EXAMPLE 6
In the greenhouse, various plants were treated at a growth height of from 2 to 24 cm with the following amounts of the following individual active ingredients and compositions thereof as emulsions and solutions:
I. ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate, 0.5, 0.75, 1 and 1.5 kg/ha;
Vi. 2-sec-butyl-4,6-dinitrophenyl acetate, 0.5, 0.75, 1 and 1.5 kg/ha;
Vii. 3,5-diiodo-4-hydroxybenzonitrile, lithium salt, 0.5, 0.75, 1 and 1.5 kg/ha;
Viii. 3,5-dibromo-4-hydroxybenzaldoxime-O-(2',4'-dinitrophenyl)-ether, sodium salt, 0.5, 0.75, 1 and 1.5 kg/ha;
Ix. 3,5-dibromo-4-hydroxybenzaldoxime-O-(2'-cyano-4'-nitrophenyl)-ether, sodium salt, 0.5, 0.75, 1 and 1.5 kg/ha;
X. 3,5-dibromo-4-hydroxybenzonitrile, sodium salt, 0.5, 0.75, 1 and 1.5 kg/ha;
Xi. .alpha.-(2-methyl-4-chlorophenoxy)-propionic acid, dimethylamine salt, 0.5, 0.75, 1 and 1.5 kg/ha;
Xii. .alpha.-(2,4-dichlorophenoxy)-propionic acid, dimethylamine salt, 0.5, 0.75, 1 and 1.5 kg/ha;
Xiii. 2,4-dichlorophenoxyacetic acid, dimethylamine salt, 0.5, 0.75, 1 and 1.5 kg/ha;
Xiv 2-methyl-4-chlorophenoxyacetic acid, dimethylamine salt, 0.5, 0.75, 1 and 1.5 kg/ha;
Xv. .alpha.(2,4,5-trichlorophenoxy)-propionic acid, dimethylamine salt, 0.5, 0.75, 1 and 1.5 kg/ha;
Xvi. 2,4,5-trichlorophenoxyacetic acid, potassium salt, 0.5, 0.75, 1 and 1.5 kg/ha;
Xvii. .gamma.-(2,4-dichlorophenoxy)-butyric acid, dimethylamine salt, 0.5, 0.75, 1 and 1.5 kg/ha;I+VI: 0.5+1, 1+0.5 and 0.75 + 0.75 kg/ha;I+VII: " "I+VIII: " "I+IX: " "I+X: " "I+XI: " "I+XII: " "I+XIII: " "I+XIV: " "I+XV: " "I+XVI: " "I+XVII: " "
After 12 to 15 days 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 ingredient VI VII VIIIkg/ha 0.5 1 0.75 1.5 0.5 1 0.75 1.5 0.5 1 0.75 1.5__________________________________________________________________________Triticum aestivum 0 0 0 0 0 10 0 20 0 0 0 10Hordeum vulgare 0 0 0 0 0 10 0 10 0 0 0 15Secale cereale 0 0 0 5 0 20 0 20 0 0 0 10Avena fatua 0 12 10 15 0 0 0 0 0 0 0 0Galium aparine 30 46 40 50 30 60 56 70 30 50 45 60Stellaria media 40 60 50 75 30 55 48 80 30 48 35 70Active ingredient IX X XI__________________________________________________________________________Triticum aestivum 0 0 0 0 5 10 7 12 0 0 0 0Hordeum vulgare 0 0 0 0 0 5 0 6 0 0 0 0Secale cereale 0 0 0 0 0 8 0 10 0 0 0 0Avena fatua 0 0 0 0 0 0 0 0 0 0 0 0Galium fatua 30 90 45 100 20 50 40 67 30 50 45 70Stellaria media 30 80 35 100 25 70 54 78 30 45 40 70Active ingredient XII XIII XIV__________________________________________________________________________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 0Avena fatua 0 0 0 5 0 0 0 0 0 0 0 0Galium aparine 50 65 58 75 10 20 15 25 10 20 15 25Stellaria media 25 55 40 75 5 10 8 20 15 20 18 35Active ingredient XV XVI I__________________________________________________________________________Triticum aestivum 0 5 0 10 0 0 0 0 0 0 0 0Hordeum vulgare 0 7 0 10 0 0 0 5 0 0 0 0Secale cereale 0 10 0 12 0 0 0 7 0 0 0 0Avena fatua 0 4 0 10 0 0 0 0 25 45 37 60Galium aparine 40 60 48 85 30 60 45 80 0 10 6 14Stellaria media 30 65 50 85 10 20 16 36 7 12 10 15Active ingredient XVII__________________________________________________________________________Triticum aestivum 0 0 0 0Hordeum vulgare 0 0 0 0Secale cereale 0 0 0 0Avena fatua 0 0 0 0Galium aparine 12 18 15 25Stellaria media 5 8 6 15__________________________________________________________________________ 0 = no damage 100 = complete destructionActive ingredient I+VI I+VII I+VIIIkg/ha 0.5+1 1+0.5 0.75+0.75 0.5+1 1+0.5 0.75+0.75 0.5+1 1+0.5 0.75+0.75__________________________________________________________________________Triticum aestivum 0 0 0 10 0 0 0 0 0Hordeum vulgare 0 0 0 10 0 0 0 0 0Secale cereale 0 0 0 20 0 0 0 0 0Avena fatua 75 85 89 64 84 77 65 86 75Galium aparine 80 80 92 100 79 100 90 80 91Stellaria media 100 92 100 100 82 98 94 81 85Active ingredient I+IX I+X I+XI__________________________________________________________________________Triticum aestivum 0 0 0 10 5 7 0 0 0Hordeum vulgare 0 0 0 5 0 0 0 0 0Secale cereale 0 0 0 8 0 0 0 0 0Avena fatua 63 83 74 66 87 76 64 85 77Galium aparine 100 82 90 89 70 86 90 80 91Stellaria media 100 84 87 100 80 100 92 83 90Active ingredient I+XII I+XIII I+XIV__________________________________________________________________________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 0Avena fatua 65 83 75 65 84 78 66 85 76Galium aparine 100 100 100 60 61 62 61 60 61Stellaria media 100 77 90 58 57 58 67 69 68Active ingredient I+XV I+XVI I+XVIII__________________________________________________________________________Triticum aestivum 5 0 0 0 0 0 0 0 0Hordeum vulgare 7 0 0 0 0 0 0 0 0Secale cereale 10 0 0 0 0 0 0 0 0Avena fatua 69 86 77 64 85 75 65 83 73Galium aparine 98 90 94 100 80 92 59 62 61Stellaria media 100 82 100 68 64 66 55 57 56__________________________________________________________________________ 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
  • a. a compound of the formula ##EQU7## wherein X denotes chloro, R denotes hydrogen or lower alkyl, R.sup.1 denotes lower alkyl and n denotes 0, 1, 2 or 3, and
  • b. a compound of the formula ##EQU8## wherein R denotes lower alkyl and R.sup.1 denotes hydrogen, or the ammonium, potassium, sodium, lithium, calcium, magnesium, ethylamine, dimethylamine, diethylamine, diethanolamine, ethanolamine, dimethylethanolamine, or trimethylamine salt of said compound in a weight ratio of a to b in the range of 2:1 to 1:2.
  • 2. A herbicide composition as claimed in claim 1 wherein compound a is ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate.
  • 3. A herbicide composition as claimed in claim 1 wherein compound a is ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate and compound b is 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide or the sodium, dimethylamine or diethanolamine salt thereof.
Priority Claims (1)
Number Date Country Kind
2336444 Jul 1973 DT
US Referenced Citations (3)
Number Name Date Kind
3598859 Yates et al. Aug 1971
3708277 Zeidler et al. Jan 1973
3846113 Fischer Nov 1974
Non-Patent Literature Citations (1)
Entry
Fischer, "Herbicidal Compositions" (1971) CA 74 No. 110714w. (1971).