DE2319377A1 - HERBICIDE - Google Patents

Description

Badische Anilin- & Soda-Fabrik AG

Our reference: O.Z. 29 828 Sws / Wil 6700 Ludwigshafen, April 12, 1973

herbicide

The present invention relates to herbicides, the mixtures contain various active ingredients.

It is known to use halocarboxylic acids, ureas and benzonitriles as selective herbicides in various crops. However, they do not always have a satisfactory herbicidal effect.

It has been found that · that herbicides that are a mixture of

a) a compound of the formula

¹ ^> NC-NC ^ '^,
R Q R ₂

in which R is a benzothiazolyl radical, one optionally substituted with identical or different individual or more substituents from the group consisting of halogen, haloalkyl, cycloalkyl, haloalkoxy, alkoxy, alkyl, alkylcarbamoyloxy, arylcarbamoyloxy, alkenylcarbamoyloxy, alkynylcarbamoyloxy, halophenoxy, alkoxyphenoxy or methoxy carboxy; a cycloalkyl or bicycloalkyl radical, an alkyl radical optionally substituted with hydroxy or halogen, R .. a hydrogen, methyl, benzoyl, cycloalkenyl or acetyloxymethyl radical, R ₂ hydrogen, alkyl, alkenyl, alkynyl, methoxy, one optionally with hydroxy or halogen-substituted alkyl radical, a carboxymethoxy or alkyl cyclohexy Ire st, R, a methyl, ethyl or ethyleneoxy radical, and with

b) a compound of the formula

RCCOR _n ,

! ti 1

X 0

in which R is halogen, alkyl, haloalkyl, X halogen, R ^ hydrogen, their salts, R, also an alkyl, haloalkyl

- 2 - OZ ₀ 29

or benzyl radical,

and or ·

c) 2,6-dichlorobenzonitrile
have a good herbicidal effect.

The mixtures can contain one or more compounds of the formula a) and one or more compounds of the formula b) and / or contain the compound c).

The mixing ratios can be chosen as desired; Mixtures of compounds of the formula a) 0.1 to J> 0 parts by weight to 0.1 to J) 0 parts by weight of b) or c) are preferred. ■

The agents according to the invention can vary in the amount used. The amount used mainly depends on the type of effect desired. The application rate is generally between 0.1 and 30 or more kg of active ingredient per hectare. The agents according to the invention can be used, inter alia, in the pre-planting method, pre-sowing method, pre-emergence method, Post-emergence process, ULV process, granulate and scattering processes, processes during emergence, entry or Multiple application processes, tank mix processes are used.

The mixtures are selective in Triticum spp., Hordeum spp ", Seeale spp., Sorghum, Zea mays, Oryza sativa, Gossypium hirsutum, Medicago sativa, Trifolium repens, Pisum sativum, Phaseolus vulgaris, Arachis spp ", Glycine Max, Beta spp", Brassica napus, Solanum tuberosum, Saccharum officinarum, Tilia spp., Alnus spp., Ulmus spp., Pyrus spp., Malus spp., Ribes spp., Berberis vulgaris, Ligustrum vulgaris, Vitis vinifera, Ananas sativus and other crops.

In addition, the mixtures can be used as a total mean in trenches, Applied to bodies of water, railway tracks, on bare land and wasteland, etc. will.

The new mixtures have a strong herbicidal effect and can therefore be used as weed killers or for

409845/1035

used to combat unwanted vegetation. Whether the new active ingredients act as total or selective agents depends mainly on the amount of active ingredient per unit area.

All are under weeds or unwanted vegetation monocotyledonous and dicotyledonous plants to understand .the in places grow up where they are not wanted.

For example, Gramineae, such as

Cynodon spp.

Digitaria spp.

Echinochloa spp.

Setaria spp.

Panicum spp.

Alopecurus spp.

LoIium spp.

Sorghum spp.

Agropyron spp.

Phalaris spp "Apera spp.

and other

Cyperaceae, like Carex spp. Cyperus spp. and other

dicot weeds, such as Malvaceae, ζ. Β. Abutilon theoprasti Sida spp. and other

Compostiae, such as Ambrosia spp. Lactuea spp. Senecio spp. Sonchus spp. Xanthium spp. 'Iva spp.

Dactylis spp. Avena spp. Bromus sppο Uniola spp. Poa spp. Leptochloa spp. Brachlaria spp. Eleusine spp. Cenchrus spp. Eragrostis spp. Phragmitres communis

Eleocharis spp. Scirpus spp.

Hibiscus spp, Malva spp.

Centaurea spp. Tussilago spp. Lapsana communis Tagetes spp. ' Erigeron spp. Aiithemis spp.

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ORIGINAL INSPECTED

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Galinsoga spp. Taraxacum spp. Chrysanthemum spp, Cirsium spp «,

Convolvulaceae such as Convolvulus spp. Ipomoea spp. and other

Cruciferae, such as Barbarea vulgar! S Brassica spp. Capsella spp. Sisymbrium spp. Thlaspi spp. Sinapis arvensis and other

Geraniaceae such as Erodium spp. and other

Portulacaceae, such as Portulaca spp "

Primulaceae such as Anagallis arvensis and other

Rubiaceae, such as Richard! A spp. Gal ium spp ",

Scrophulariaceae such as Linaria spp. Veronica spp.

Solanaceae such as Physalis spp. Solanum spp. and other

Urticaceae such as Urtica spp. Matricaria spp " Artemisia spp. Bidens spp. and other

Cuscuta sppο Jaquemontia tamnifolia

Arabidopsis thaliana Descurainia spp. Draba spp. Coronopus didymus Lepidium spp »Raphanus spp.

Geranium spp

and other

Lysimachia spp.

Diodia spp. and other

Digitalis spp. and other

Nicandra spp. Datura spp.

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Violaceae, such as Viola spp _o

Zygophyllaceae such as Tribulus terrestis

Euphorbiaceae such as Mereurialis annua

Umbelliferae such as Daucus carota Aethusa cynapium

Commelinaeae Commelina spp.

Labiatae, such as Lamium spp _e and others

Leguminosae such as Medicago spp. Trifolium spp. Vicia sppο and others

Plantaginaceae such as Plantago spp _o

Polygonaceae such as Polygonum spp. Rumex spp ₀

Aizoaceae, such as Mollugo verticiliata

Amaranthaceae, such as Amaranthus spp »

Boraginaeeae such as Amsinckia spp. Myostis spp. and other

Caryophyllaceae such as - Stellaria spp. Spergula spp. and other and other Euphorbia spp.

Ammi majus and other and other Galeopsis spp.

Sesbania exaltata Cassia spp. Lathyrus spp "

and other

Pagopyrum spp. and others and others and others

Anchusa spp. Lithosperum spp.

SiIene spp. Cerastium spp,

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Saponaria spp. Seieranthus annuus

Chenopodiaceae such as Chenopodium spp. Kochia sppο Salsola potash

Lythraceae such as Cuphea spp _o

Oxalidaceae such as Oxalis spp.

Ranunculaeeae such as Ranunculus spp. Delphinium spp.

Papaveraceae, such as Papaver sppο and other

Onagraceae such as Jussiaea spp.

Rosaceae such as Alchemillia spp. and other

Potamogetonaceae such as Potamogeton spp.

Najadaceae, such as NaJ as spp.

Equisetaceae Equisetum spp.

Marsileaceae, such as Marsilea quadrifolia

Polypodiaceae, Pteridium quilinum

Alisamtaceae Alisma spp.

and others are fought. Agrostemma pallida and others

Atriplex spp. Monolepsis nuttalliana and other

and other

• Adonis spp-. and other

Fumaria officinalis

and other Potentilla spp.

and others and others and others and others

Sagittaria sagittifolia

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The application takes place ζ. B. in the form of directly sprayable Solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, grit, granules by spraying, misting, dusting, scattering or watering. The forms of application depend entirely on the intended use; in any case, they should ensure the finest possible distribution of the active ingredients according to the invention.

For the production of directly sprayable solutions, emulsions, pastes and oil dispersions, mineral oil fractions are used by medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils etc., as well as oils of vegetable or of animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B. benzene, toluene, xylene, paraffin, Tetrahydronaphthalene, alkylated naphthalenes or their derivatives, e.g. B. methanol, ethanol, propanol, butanol, chloroform, Carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., strongly polar solvents such as. B. dimethylformamide, Dimethyl sulfoxide, N-methylpyrilidone, water, etc. into consideration.

Aqueous use forms can consist of emulsion concentrates, pastes or wettable powders (wettable powders), oil dispersions can be prepared by adding water. The substances can be used to produce emulsions, pastes or oil dispersions as such or dissolved in an oil or solvent, homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers · It can also consist of active substances, wetting agents, adhesives, dispersants or emulsifiers and possibly Solvent or oil existing concentrates are prepared, which are suitable for dilution with water.

The following surface-active substances should be mentioned: alkali, alkaline earth, Ammonium salts of ligninsulphonic acid, naphthalenesulphonic acids, phenolsulphonic acids, alkylarylsulphonates, alkylsulphates, Alkyl sulfonates, alkali and alkaline earth salts of dibutylnaphthalene sulfonic acid, Lauryl ether sulfate, fatty alcohol sulfates, fatty acid alkali and alkaline earth salts, sulfated salts

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ter hexadecanols, heptadecanols, octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated! Naphthalene and naphthalene derivatives with Formaldehyde, condensation products of naphthalene or the Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, - octylphenol, - Nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, Fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, Lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulphite waste liquors and methyl cellulose.

Powder, litter and dust can be produced by mixing or grinding the active substances with one solid carrier material are produced.

Granules, e.g. coating, impregnation and homogeneous granules, can by binding the active ingredients to solid carriers getting produced. Solid carriers are e.g. B. Mineral earths such as silica gel, silicic acids, silica gels, silicates, Talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, Magnesium oxide, ground plastics, fertilizers, such as. B. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as grain flours, tree bark, wood and nut shell flour, cellulose powder and other solid carriers e.

The formulations contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90 percent by weight.

Oils of various types, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, antifoams (e.g. silicones), growth regulators, antidotes or other herbicidally active compounds, such as e.g. B. substituted anilines
substituted aryloxycarboxylic acids and their salts, esters and

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substituted ethers substituted arsonic acids and their salts, esters and amides substituted benzimidazoles substituted benzisothiazoles substituted benzthiadiazinone dioxides substituted benzoxazines substituted benzoxazinones substituted benzthiadiazoles substituted biurets substituted quinolines substituted carbamates substituted aliphatic carboxylic acids and their salts, Ester and amide-substituted aromatic carboxylic acids and their salts, esters and amides substituted carbamoylalkyl thiol or dithiophosphates substituted quinazolines, substituted cycloalkylamidocarbon thiol acids and their Salts, esters and amides of substituted cycloalkylcarbonamido-thiazoles substituted dicarboxylic acids and salts, esters and amides substituted dihydrobenzofuranylsulfonates substituted disulfides substituted dipyridylium salts substituted dit thiocarbamates substituted dithiophosphoric acids and their salts, esters and amides

substituted ureas substituted hexahydro-1-H-earbothioate substituted hydantoins substituted hydrazides substituted hydrazonium salts substituted isooxazole pyrimidones substituted imidazoles substituted isothiazole pyrimidones substituted ketones substituted naphthoquinones substituted aliphatic nitriles substituted aromatic nitriles

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substituted oxadiazoles · substituted oxadiazinones substituted oxadiazolidinediones substituted oxadiazinediones 'Substituted phenols and their salts and esters substituted phosphonic acids and their salts, esters and Amides

substituted phosphonium chlorides substituted phosphonalkylglyzines substituted phosphites substituted phosphoric acids and their salts, esters and Amides

substituted piperidines substituted pyrazoles substituted pyrazole alkylcarboxylic acids and their salts, Ester and amide substituted pyrazolium salts substituted pyrazolium alkyl sulfates substituted pyridazines substituted pyridazones substituted pyridinecarboxylic acids and their salts, esters and amides

substituted pyridines substituted pyridine carboxylates substituted pyridinones substituted pyrimidines substituted pyrimidones substituted pyrrolidinecarboxylic acids and their salts, esters and amides

substituted pyrrolidines substituted pyrrolidones substituted arylsulfonic acids and their salts, esters and Amides

substituted styrenes substituted tetrahydro-oxadiazinediones substituted tetrahydro-oxadiazole dione substituted tetrahydromethanoindenes substituted tetrahydro-diazol-thiones substituted tetrahydro-thiadiazine-tnions

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substituted tetrahydro-thiadiazole diones substituted aromatic thiocarboxamides substituted thiocarboxylic acids and their salts, esters and

substituted thiol carbamates

substituted thioureas

substituted thiophosphoric acids and their salts, esters and

substituted triazines

substituted triazoles

substituted uracils

substituted uretidinediones

if necessary, only added immediately before use (tank mix). The last-mentioned herbicidal compounds can also be used before or after the individual active ingredients or mixtures according to the invention.

These agents can be admixed with the herbicides according to the invention in a weight ratio of 1:10 to 10: 1. That The same applies to oils, fungicides, nematocides, insecticides, bactericides, antidotes and growth regulators.

The compounds N- (2-benzthiazolyl) -N ¹ -methylurea became in the greenhouse and in the field

N- (2-Benzthiazolyl) -N-methyl-N ^! -methylurea N- / 3- (N-tert.Butylcarbamoyloxy) -pheny ^ -N ¹ -methylurea N- / 3- (N-tert .Butylcarbamoyloxy) -pheny ^ -N ¹ , N ¹ - dimethyl urea off N-phenyl -N ', N ¹ -dimethylurea

Np-chlorophenyl-N ', N'-dimethylurea Np-chlorophenyl-N' -methyl-N ¹ -butyn- (1) -yl- (3) -urea Nm-trifluoromethylphenyl-N ^f , N ¹ -dimethylurea Np-trifluoromethylphenyl -N ', N' -dimethylurea Ν- / Ϊ- (4 * -Glorophenoxy) -pheny] 7-N ^l , N ^! -dimethylurea N - /? - (4 ¹ -Methoxyphenoxy) -phenyj7-N ^f , N ¹ -dimethylurea N-4-fluorophenyl-N ¹ -carboxymethoxy-N ¹ -methylurea f N - ^^ - dichlorophenyl-N-benzoyl- N ', N * -dimethylurea N ~ 3-chloro-4-methylphenyl-N ^! , N ¹ -dimethylurea, N-3-chloro-4-methoxyphenyl-N ^t , N ¹ -dimethylurea, N-3,4-dichlorophenyl-N ', N ¹ -dimethylurea

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N-3,4-dichlorophenyl-N'-methyl-N'-n-butylurea f N-3,4 ~ dichlorophenyl-N'-methylurea N-3,4-diehlophenyl-N ', N'-diethylurea N-phenyl -N-benzoyl-N ', N' -dimethylurea f N, N'-bis- (1-hydroxy-2,2,2, -trichloroethyl) -urea N-4-chlorophenyl-N-benzoyl-N ', N '-dimethylurea N-4-methoxyphenyl-N-benzoyl-N', N ^r -dimethylurea N- / 5- (N-methyl-N-phenylcarbamoyloxy) -phenyl7-N ^! , N '-dimethylurea Np-bromophenyl-N'-butin-1-yl- (3) -N ^! -methylurea NJ-chloro - ^ - trifluoromethylphenyl-N ¹ , N'-dimethylurea ■ N-4-cyclopropyl-phenyl-N ', N'-dimethylurea N-Xl ¹ , 1', 2 ', 2'-tetrafluoroethoxy) - phenyl-N ', N'-dimethylurea N-4-butoxyphenyl-N' -methylurea f NJ- (I ', 1' , 2'-trifluoro-2-chloroethoxy) -phenyl-N'-methyl-N'-methoxyurea N-4-chlorophenyl-N'-methyl-N'-methoxyurea N-3,4-dichlorophenyl-N'-methyl-N ¹ -methoxyurea N-4-bromophenyl-N'-methyl-N ^! methoxyurea N-3-chloro-4-bromophenyl-N'-methyl-N ^! methoxyurea N-3-chloro-4-methoxyphenyl-N'-methyl-N'-methoxyurea N-phenyl-N'-methyl-N'-methoxyurea Nm-trifluoromethyl-phenyl-N-cyclohex-1-enyl-N ¹ , N'-dimethylurea Nm-trifluoro-methyl-phenyl-N-cyclohex-1-enyl-N * -methylurea f N-3 * 4-dichlorophenyl-N-cyclohex-1-enyl-N '/ N' -dimethylurea N-3-trifluoromethyl-phenyl-N-cyclooctenyl-N ', N' -dimethylurea Nm-chlorophenyl-N-cyclohex-l-enyl-N ', N'-dimethylurea N-phenyl-N-cyclohex-1-enyl- N ', N'-dimethylurea Nm-trifluoromethylphenyl-N-cyelooctenyl-N ¹ -methylurea f Nm- chlorophenyl-N-cyclohex-1-enyl-N ¹ -methylurea f N-phenyl-N-cyelohex-1-enyl- N'-methylurea Np-fluorophenyl-N-cyelohex-1-enyl-N'-methylurea N-3-chloro-4-methoxy-phenyl-N-cyelohex-1-enyl-N'-methylurea f N-3-chlorine -4-methoxy-phenyl-N-cyclohex-l-enyl-N ', N'-dimethylurea N-3-trifluoromethyl-phenyl-N-acetyloxymethyl-N', N'-dimethylurea N- Ij) - (<* , tf-Dimethyl-propen- 1-yl- (3) -carbamoyloxy) -phenyl7-N '* N' -

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dimethyl urea

N-cyelooctyl-N ', N ^f -dimethylurea

Ν- / Ϊ- or 2- (3a, 4.5 _J 6,7,7a-hexahydro-4,7-methanoindanyl_) 7-N ', N "' - dimethylurea

N- / 5- (3a, 4,5,6,7,7a-hexahydro-4,7-methanoindanylJ7-N ^t , N 'dimethyl urea

N-bicyclo- (3,3,0) -octyl-N ', N'-dimethylurea N- / T- or 2- (3a, 4,5,6,7,7a-hexahydro-4,7-methanoindanyl) 7-N-eyelohex-1-enyl-N ', N'-dimethylurea Ν- / Ϊ- or 2- (3a ₅ 4,5,6,7,7a-hexahydro-4,7-methanoindanyl) 7-N- cyclohex-l-enyl-N'-methylurea

N-5-chloro-4-methylphenyl-N-cyclohex-1-enyl-N ', N ^f -dimethylurea

N-5-chloro-4-methy.lphenyl-N-cyclohex-1-enyl-N'-methylurea N-3-methyl-4-chlorophenyl-N-cyclohex-1-enyl-N ¹ -methylurea N-3- Methyl-4-chlorophenyl-N-cyclohex-1-enyl-N ¹ , N '-dimethylurea

N-> methyl-4-chlorophenyl-N ', N' -dimethylurea N- 3- methyl-4-chlorophenyl-N'-methylurea N-5-methyl-4-chlorophenyl-N'-methyl-N'-methoxyurea N -3-chloro-4-methylphenyl-N ^! -methyl-N ¹ -methoxyurea N- J> - chloro-4-methylphenyl-N'-methylurea f NJ-chloro-4-trifluoromethoxyphenyl-N ¹ , N'-dimethylurea N-3-chloro-4-methoxyphenyl-N '-methylurea N-4-chloro-3-methoxyphenyl-N', N'-dimethylurea N-4-chloro-3-methoxyphenyl-N ^T -methyl-N'-methoxyurea N-4-chloro-3-methoxyphenyl-N '-methylurea methyl 2- (j5,> -diethylenoxyurea) benzoate', dt-dichloropropionic acid, sodium salt
o'iCK dichlorobutyric acid sodium salt
ας B ₃ ß-trichloropropionic acid sodium salt trichloroacetic acid sodium salt
2,2,313-tetrafluoropropionic acid sodium salt. OC ₃ (ji-dichloropropionic acid benzyl ester
^, oi-dichloropropionic acid-ß-chloroethyl ester 2,6-dichlorobenzoic acid nitrile

tested in a mixture with each other on the plants already mentioned. The application rates were in each case 0.1 to 50 kg / ha of active ingredient and more.

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The agents listed have a biological effect corresponding to that of the compounds listed in Examples 1 to 12.

example 1

An agricultural area was sown with various seeds «Immediately afterwards the soil prepared in this way was created treated with the following individual active ingredients and their mixtures as a dispersion:

I N-3-chloro-4-methoxyphenyl-N'-methyl-N ¹ -methoxyurea f

II N-> chloro-4-methylphenyl-N ', N' -dimethylurea f

III 2,6-dichlorobenzonitrile

with 0.1, 0.3, 0.5 and 0.6 kg / ha of active substance

I + III 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha of active substance II + III 0.1+ 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha of active substance.

After 3 to 4 weeks it was found that the mixtures had a better herbicidal action with the same tolerance the crops showed as the active ingredients I, II and III.

The test result can be seen from the following table.

Active ingredient
kg / ha of active substance '0.1 0.3 I.
0.5 0.6 0.1 0, II
3 0.5 0.6 Useful plants: Hordeum vulgar 0 0 0 0 0 0 0 0 Tritieum aestivum 0 0 0 0 0 0 0 0 Secale cereale 0 0 0 0 0 0 0 0 unwanted plants: Alopecurus myosuroides . 7th 20th 30th 35 10 25th 31 40 Avena fatua 5 15th 25th 30th 5 15th 26th 30th Poa annua 5 15th 25th 30th 5 15th 26th 31 Atriplex spp. 10 23 30th 40 12th 30th 44 50 Galium aparine 5 12th 15th 20th 5 16 25th 32 Lamium amplexicaule 15th 30th 46 52 15th 30th 45 50 Matricaria chamomilla 10 28 40 50 15th 37 50 60 Polygonum aviculare 5 16 26th 32 8th 20th 38 43 Polygonum persicaria 15
40984 20th
5/1 34
03 4o
5 10 30th 42 46
/ 1R

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Active ingredient 0.1 0.3 III 0.6 I. + III 0.3 0, II + III kg / ha a. S. 0.5 0.1 0.5 0.3 ⁰ I. 1 0.5 0.3 0.5 0.1 5 0.1 0.3 Useful plants: 0 0 0 0 0 Hordeum vulgar 0 0 0 0 0 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 0 0 0 0 0 Seeale, cereale 0 0 0 0 0 unwanted plants: 10 20th 45 70 77 Alopecurus myosuroides 12th 25th 40 48 75 68 68 80 70 73 Avena fatua 5 15th 46 52 78 65 56 78 70 68 Poa annua 15th 37 45 60 77 58 89 88 58 58 Atriplex spp. 13th 30th 50. 50 85 73 73 75 90 95 Galium aparine 12th 25th 42 40 78 60 79 78 67 73 Lamium amplexicaule 8th 20th 34 40 77 74 78 80 85 80. Matricaria chamomilla 15th 36 35 60 73 76 80 83 85 83 Polygonum aviculare 20th 55 ' 50 78 85 70 · 97 98 81 87 Polygonum persicaria 70 98 82 90 98

0 = without damage
100 = total damage

Example 2

In the field, various plants were grown to a height of 2 to 22 cm with the following individual active ingredients and their mixtures treated as an oil dispersion:

I. N-3-chloro-4-methoxyphenyl-N ^l -methyl-N ^t -methoxyurea

II N-3-chloro-4-methylphenyl-N ^T , N ¹ -dimethylurea

III 2,6-dichlorobenzonitrile

with 0.1, 0.3, 0.5 and 0.6 kg / ha a. S. I + III 0.1+ 0.5, 0.5 +0.1 and 0.3 + 0.3 kg / ha a. S. II + III 0.1 + 0.5, 0.5 + 0.1 and 0.3 + 0.3 kg / ha a. S.

After 2 to 3 weeks it was found that the mixtures showed a better herbicidal effect with the same tolerance on the crop plants than the individual active ingredients. ·

The test result can be seen from the following table.

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Active ingredient 0.1 0.3 I. 0.5 0.6 0.1 0, II 0.6 kg / ha a. S. 3 0.5 Useful plants: 0 0 0 0 0 0 0 Hordeum vulgar 0 0 0 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 0 0 0 Seeale cereale 0 unwanted plants: 28 50 6o 64 10 20th 48 Alopecurus myosuroides 12th 32 35 40 10 20th 35 42 Avena fatua 21 52 60 68 15th 40 36 65 Poa annua 20th 47 58 64 15th 40 61 64 Atriplex spp ₀ 5 20th 25th 26th 2 6th 60 12th Galium aparine 10 26th 30th 37 10 30th 10 52 Lamium amplexicaule 10 25th 30th 35 15th 38 45 53 Matricaria chamomilla 5 17th 28 30th 8th 20th 46 35 Polygonum aviculare 9 25th 30th 34 10 20th 30th 48 Polygonum persicaria 10 15th 25th 29 10 17th 45 32 Apera spiea venti 28

Active ingredient 0.1 III 0.5 0.6 0.1 I + III II + III kg / ha a. S. 0.3 0 ^ 5 0.5 0.3 0.1 0.5 0.3 0.1 0.3 0.5 0.1 0.3 Useful plants: 0 0 0 0 Hordeum vulgar 0 0 0 0 0 0 0 0 0 0 Triticum aesticum 0 0 0 0 0 0 0 0 0 0 Seeale cereale 0 0 0 0 0 0 unwanted plants: 15th 45 53 98 Alopecurus myosuroides 15th 35 50 63 89 99 100 82 78 82 Avena fatua 5 35 45 50 92 75 98 85 80 82 Poa annua 10 20th 60 65 98 90 97 88 75 88 Atriplex spp. 12th 50 42 46 77 97 100 97 98 100 Galium aparine 20th 33 55 63 94 82 80 70 50 68 Lamium amplexicaule 10 40 35 40 72 77 93 9> 90 97 Matricaria ehamomilla 20th 21 70 75 98 68 73 79 89 96 Polygonum aviculare 18th 60 42 50 79 76 100 99 78 98 Polygonum persicaria 15th 33 68 75 100 80 85 78 88 80 Apera spica venti 36 76 80 100 78 79

0 = without damage

100 = total damage \

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Example 3

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In the greenhouse, test vessels were filled with loamy sandy soil and sown with various seeds «After that, the soil prepared in this way was given the following individual active ingredients and their Mixtures treated as granules:

I N -3-chloro-4-methoxyphenyl-N ^t -methyl-N'-methoxyurea III 2,6-dichlorobenzonitrile

with 0.1, 0.3, 0.5 and 0.6 kg / ha a. S. I + III 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha a. S.

After 3 to 4 weeks it was found that the mixture had a better herbicidal effect with the same tolerance to the Crop plants showed as the active ingredients I and III.

The test result can be seen from the following table.

Active ingredient
kg / ha a. S, 0.1 7th 0.3 I.
0.5 0.6 0.1 III
0.3 0.5 0 0.6 ο, I + III
1 0.5 0.3 5 0 ο * 5 0.1 0.3 Useful plants: 5 0 Hordeum vulgar 0 10 0 0 0 0 0 0 0 0 0 Triticum aestivum 0 5 0 0 0 0 0 40 0 0 0 0 Seeale cereale 0 15th 0 0 0 0 0 46 0 0 0 0 unwanted plants: 10 45 Alopecurus
myosuroides 5 20th 30th 35 10 20th 50 45 75 70 69 Avena fatua 15th 15th 25th 30th 12th 25th 42 48 80 67 69 Poa annua 15th 25th 30th 5 15th 34 52 77 58 60 Atriplex spp. 23 30th 40 15th 37 35 60 88 73 78 Galium aparine 12th 15th 20th 13th 30th 50 50 75 58 70 Lamium amplexicaule 30th 46 52 12th 25th 70 40 74 87. 83 Matricaria chamomjlla 28 40 50 8th 20th 40 73 76 75 Polygonum aviculare 16 26th 32 15th 36 60 83 70 80 Polygonum ρersicaria 20th 34 40 20th 55 -78 100 79 98

0 = without damage
100 = total damage

409845/1035

/ 18th

Example 4

O.Z. 29 828

Various plants were grown at one height in the greenhouse from 2 to 25 cm treated with the following individual active ingredients and their mixtures as an emulsion:

I N - ^ - chlorine - ^ - methoxvphenyl-N'-methyl-N'-methoxyurea f III 2,6-dichlorobenzonitrile

with 0.1, 0.3, 0.5, 0.6 kg / ha a. S. I + III 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha a. S.

After 2 to 3 weeks it was found that the mixture had a better herbicidal effect with the same tolerance the crops showed as the single active ingredients.

The result of the experiment can be seen in the table below.

Active ingredient
kg / ha a. S. 0.1 28 O, I.
3 0.5 0.6 0.1 0, III
3 0.5 0.6 0, I + III
1 0.5 0.3 12th 0 * 5 0.1 0.3 Useful plants: 21 Hordeum vulgar 0 20th 0 0 0 0 0 0 0 0 0 0 Trltieum aestivum 0 5 0 0 0 0 0 0 0 0 0 0 Seeale cereale 0 10 0 0 0 0 0 0 0 0 0 0 unwanted plants: 10 Alopecurus
myosuroides 5 50 6o 64 15th 35 45 53 90 98 100 Avena fatua "10 32 35 40 15th 35 50 63 75 76 92 Poa annua 52 60 68 5 20th 45 50 92 94 90 Atriplex spp. 47 58 64 10 50 60 65 90 93 100 Galium aparine 20th 25th 26th 12th 33 42 46 73 64 80 Lamium amplexicaule 26th 30th 37 20th 40 55 63 90 80 92 Matricaria
chamomilla 25th 30th 35 10 20th 35 41 75 .68 73 Polygonum aviculare 15th 28 30th 20th 60 70 75 98 79 97 PolygonunLpersicaria 25th 30th 35 18th 33 42 55 78 77 83

0 = without damage
100 = total damage

409 845/1035

O.Z. 29 828

Example 5

An agricultural area became different before the emergence Weeds and grass weeds with the following individual active ingredients and their mixtures treated as a paste:

III 2,6-dichlorobenzonitrile

IV "', tf-dichloropropionic acid sodium salt

with 0.1, 0.3, 0.5 and 0.6 kg / ha a. S.
Ill + IV 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha a. S.

After 3 to 4 weeks it was found that the mixture
a better herbicidal effect with the same tolerance
on the cultivated plants showed as the individual active ingredients III and IV.

The test result can be seen from the following table:

Active ingredient 0.1 8th III, 0.5 0.6 0.1 IV 5 0.5 0.6 III + IV 0.5 0.3 kg / ha 12th o, 3 0.3 15th 0.1 0.1 .8th 0 0.5 Useful plants: 0 15th 0 0 0 15th 0 0 0 0 Berberis vulgaris 0 20th 0 0 0 0 0 2 0 0 0 0 0 Ligustrum vulgar unwanted plants: 12th 0 0 5 0 Agropyron spp _e 10 26th 30th 0 20th 10 10 55 52 Lamium amplexicaule 8th 19th 34 40 5 28 24 28 50 73 70 Matricaria
chamomilla 25th 35 40 0 5 5 62 64 50 Atriplex spp. 20th 50 60 5 27 35 45 82 78 Polygonum persicaria 37 70 78 0 5 5 70 97 85 Melilotus albus 55 37 43 0 9 10 55 65 63 Echinochloa crus-
galli 28 40 46 5 44 50 50 73 75 LoIium perenne 25th 35 41 10 42 46 80 75 76 20th 78

0 = without damage
100 = total damage

409845/1035

/ 20

Example 6

O.Z. 29 828

In the field, various undesirable plants were found in one Growth height of 3 to 25 cm with the following individual active ingredients and their mixtures treated as dust:

III 2,6-dichlorobenzonitrile

IV Λ, uiT-Di chloropropionic acid sodium salt

with 0.1, 0.3, 0.5 and 0.6 kg / ha a. S. III + IV 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha a. S.

After 2 to 3 weeks it was found that the mixture had a better herbicidal effect with the same tolerance to the Crops showed as the single active ingredients.

The "test result" can be seen in the table below.

Active ingredient 0.1 III 0.5 0.6 0.1 IV 0.5 0.6 III + IV 0.5 0.3 kg / ha a. S. 0.3 0.3 0.1 0.1 0.3 0.5 Useful plants: 0 0 0 0 0 0 0 0 Berberis vulgar! S 0 0 0 0 0 0 0 0 0 0 0 Ligustrum vulgar . 0 0 0 unwanted plants 10 33 39 12th 40 45 73 83 Agropyron spp 20th 25th 55 63 10 33 38 45 78 89 86 Lamium amplexicaule 10 40 35 40 0 20th 3 5 82 63 50 Matricaria chamo-
milla 10 20th 60 65 5 · 0 40 46 45 88 93 Atriplex spp. 18th 50 42 50 15th 20th 37 44 80 83 87 Polygonum persicaria 10 33 45 52 5 27 35 40 80 78 73 Melilotus albus 10 30th 45 49 10 15th 50 54 71 80 82 Echinochloa
crus-galli 5 28 30th 31 6th 26th 37 43 86 65 67 Lolium perenhe 19th 20th 70

0 = without damage
100 = total damage

409845/1035

Example 7

O.Z. 29 828

An agricultural area became different before the emergence Weeds and grass weeds treated as granules with the following individual active ingredients and their mixtures:

I N-J5-chloro-4-methoxyphenyl-N'-methyl-N'-methoxyurea

II NJ-chlorine - ^ - methylphenyl-N ', N ^l -dimethylurea IV «, cC-dichloropropionic acid sodium salt

with 0.1, 0.3, 0.5 and 0.6 kg / ha a. S. I + IV 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha a. S. II + IV 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha a. S.

After 3 to 4 weeks it was found that the mixtures showed a better herbicidal effect with the same tolerance on the crop plants than the active ingredients I, II and IV.

The test result can be seen from the following table.

Active ingredient 0.1 5 0.3 I. 0.5 0.6 0.1 5 II 0.5 0.6 kg / ha a. S. 5 7th 0.3 Useful plants: 0 0 0 0 0 0 0 0 0 Pyrus spp. 0 15th 0 0 0 0 15th 0 0 0 Malus spp. «
• 5 8th 0 unwanted plants 15th 20th 26th 35 10 15th 20th Cirsium arvense 16 28 34 10 26th 30th Equisetum spp. 10 15th 18th 18th 10 20th Echinochloa crus-gaUi 30th 46 52 10 45 50 Lamium amplexicaule 18th 30th 40 30th 38 43 Lolium perenne 20th 34 40 25th 42 46 Polygonum persicaria 30th

409845/1035

/ 22

U. it »cy ucu

Active ingredient 0.1 0 0, 5 IV 0.6 O, I + IV 0.3 0, II + IV 0.3 kg / ha a. S. 5 3 3 0.5 ° l 1 0.5 0.3 0, 1 0.5 0.3 5 0.1 5 0.1 Useful plants: 0 5 0 20th 0 0 0 0 0 Pyrus spp. 0 5 0 15th 0 0 0 0 0 0 0 0 Malus spp. . 10 28 0 0 0 unwanted plants 0 2 15th 45 54 45 45 Cirsium arvense 10 10 .43 55 58 45 43 50 Equisetum spp " .8th 58 54 Echinochloa crus- 50 72 60 72 58 galli 44 28 66 50 72 67 50 72 Lamium amplexicaule 24 46 - 75 77 • 75 77 79 80 Lolium perenne 42 5 50 68 50 45 76 60 Polygonum persicaria 5 62 70

0 = without damage
100 = total damage

Example 8

In the field, various undesirable plants at a height of 0.5 to 12 cm with the following individual active ingredients and ' their mixtures treated as granules:

I N -3-chloro-4-methoxyphenyl-N'-methyl-N ^T -methoxyurea

II N-3-chloro-4-methylphenyl-N ¹ , N'-dimethylurea IV o ^ a-dichloropropionic acid, sodium salt

with 0.1, 0.3, 0.5 and 0.6 kg / ha a. S. I + IV. 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha a. S. II + IV 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha a. S.

After 2 to 3 weeks it was found that the mixtures had a better herbicidal effect with the same tolerance to the Cultivated plants showed as the single active ingredients.

The test result can be seen from the following table.

409845/1035

O.Z. 29 828

Active ingredient 0.1 5 0.3 I. 0.5 0.6 0.1 8th II 0.5 0.6 kg / ha a. S. 7th 5 0.5 Useful plants: 0 0 0 0 0 0 0 Pyrus spp. 0 15th 0 0 0 0 14th 0 0 0 Malus spp. 10 10 0 unwanted plants: 10 18th 24 27 8th 55 42 Cirsium arvense 9 17th 25th 51 10 25th 27 52 Equisetum spp. 15th Echinochloa crus- 50 45 50 45 50 galli 26th 50 57 50 45 52 Lamium atnplexicaule 25th 57 45 50 28 55 Lolium perenne 25th 50 54 20th 45 48 Polygonum persicaria 20th

Active ingredient 0.1 5 IV 0.5 0.6 0.1 I + IV 0.3 0.1 II + IV 0.3 kg / ha a. S. 8th 0.5 0.5 0.5 0.3 0.5 0.5 0.3 10 0.1 0.1 Useful plants: 0 0 0 0 0 0 0 Pyrus spp. 0 10 0 0 0 0 0 0 0 0 0 Malus spp. i: 6th 0 0 0 unwanted planters 15th 27 32 61 62 62 70 Cirsium arvense 15th 40 68 58 64 70 68 62 Equisetum spp. 19th 50 54 90 60 84 88 62 82 Echinochloa crus-. 26th 80 80 galli 58 45 77 73 76 77 Lamium amplexicaule 20th 37 43 75 68 72 73 81 68 Lolium perenne 20th 37 44 73 70 79 74 63 74 Polygonum persicaria 27 73 85

0 = without damage
100 = total damage

409845/1035

Example 9

O.Z. 29 828

2313377

An agricultural area became different before the emergence unwanted plants with the following individual active ingredients and their mixtures treated as granules:

III 2,6-dichlorobenzonitrile

IV α, Λ-dichloropropionic acid sodium salt with 0.1, 0.3, 0.5 and 0.6 kg / ha each

III + IV 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha a. S.

After 3 to 4 weeks it was found that the mixture had a better herbicidal effect with the same tolerance to the Crop plants showed as the active ingredients III and IV.

The test result can be seen from the following table:

Active ingredient 0.1 9 O, III 0.6 0.1 0 0.3 5 IV 0.6 0, III + IV 0.3 kg / ha a. S. 3 0.5 0.5 0, 1 0.5 0.3 10 5 20th 5 0.1 Useful plants: 0 8th 0 0 0 0 0 3 0 0 0 Tilla spp. 0 13th 0 0 0 0 0 0 0 0 0 0 0 0 Alnus spp. unwanted plants: 12th 0 20th 35 0 0 Cirsium arvense 25th 41 15th 58 60 Echinochloa crus- 37 10 65 galli 25th 46 50 80 73 Equisetum spp. 23 40 34 44 10 45 74 55 Galium aparine 30th 30th 50 8th 7th 48 60 59 Bromus tectorum 28 42 41 5 50 80 70 88 37 42 83

0 = without damage
100 = total damage

409845/1035

O.Z. 29 828

Example 10

In the field, various undesirable plants with a height of 2 to 10 cm with the following individual active ingredients and whose mixture is treated as a dispersion:

III 2,6-dichlorobenzonitrile

IV octf-dichloropropionic acid sodium salt 0.1, 0.3, 0.5 and 0.6 kg / ha a. S.

III + IV 0.1 + 0.5, 0.5 + 0.1, 0.3 + 0.3 kg / ha a. S.

After 2 to 3 weeks it was found that the mixture had a better herbicidal effect with the same tolerance on the crops showed as the individual active ingredients.

The test result can be seen from the following table.

Active ingredient 0.1 7th III 0.5 0.6 0.1 5 IV 0.5 0.6 0, III + IV 0.3 kg / ha a. S. 0.3 0.3 O, 1 0.5 0.3 10 10 5 ο, ι Useful plants: 0 10 0 0 0 8th 0 0 0 0 Tilia sppο 0 12th 0 0 0 0 5 0 0 0 0 0 0 Alnus spp. unwanted plants: 10 0 12th 0 0 Cirsium arvense 30th 34 27 32 59 65 Echinochloa 23 15th 62 crus-galli 45 49 50 54 64 77 Equisetum spp. 28 35 40 26th 36 40 73 79 72 Galium aparine 26th 42 46 19th 20th 23 60 70 70 Bromus tectorum 33 35 40 10 38 42 73 75 83 26th 31 80

0 = without damage
100 = total damage

409845/1035

Example 11

■ O.Z. 29 828

2313377

In the greenhouse, test vessels were filled with loamy sandy soil and sown with seeds from various undesirable plants. The soil prepared in this way was then treated as granules with the following individual active ingredients and their mixtures: I N - ^ - chlorine - ^ - methoxyphenyl-N '-methyl- N '.- methoxyurea f III 2,6- Di chi orb enz oni tril
TV «, a-dichloropropionic acid sodium salt

with 1, 5 and 6 kg / ha a. S.
I + III + rV 1 + 1 + 5, 1 + 5 + 1, 5 + 1 + 1 kg / ha a. S.

Then the planting with Vitis vinifera took place.

After 3 to 4 weeks the mixture was found to have a showed better herbicidal effect with the same tolerance on the crop than the active ingredients I, III and IV.

The test result can be seen from the following table.

Active ingredient 1 I. 6th 1 III 6th 1 IV 6th kg / ha a «, S ₀ 5 VJl 5 Useful plant: 0 0 0 0 0 0 Vitis vinifera • 0 O 0 unwanted plants 12th 65 10 60 3 25th Sonchus spp. 15th 57 70 15th 56 80 0 20th 15th Convolvulus arvensis 2 60 25th 55 68 100 12th 10 50 Agropyron repens 12th 20th 74 14th 80 70 18th 40 85 Digitarla sanguinaHs 63 62 67

Active ingredient 1 + 5 + 1 I + III + IV 85 kg / ha a. S- « 5 + 1 + 1 1 + 1 + 5 80 Useful plant: 0 Vitis vinifera 0 0 unwanted plants: 100 Sonchus spp. 100 100 Convolvulus arvensis 100

409845/1035

- S. 27 - I + III + IV O.Z. 29 828 r ep ens 1 + 5 + 1 5 + 1 + 1 2319377 Active ingredient sanguinalis 100 100 kp / ha a. 100 100 1 + 1 + 5 Agropyron 100 Digitaria 100

0 = without damage
100 = total damage

Example 12

A wasteland with a population of Carex spp., Phragmites communis and Typa spp. was at a height of vegetation from 20 to 50 cm each with 7 * 5 kg / ha of active substance Single active ingredients

N-3-chloro-4-methoxyphenyl-N'-methyl-N ¹ -methoxyurea I, 2,6-dichlorobenzonitrile III and

«, Ä-dichloropropionic acid sodium salt IV as well as their mixture I + III '+ IV with 2.5 + 2.5 + 2.5 kg / ha of active substance, each dispersed in 500 liters of water per ha, treated.

After 2 to 5 weeks it was found that the mixture

1 + III + IV achieved a 100% kill, while the individual components only showed damage of 50 to 80%.

/ 28 409845/1035

Claims (1)

-28 - O.Z. 29 828 Claim Herbicide containing a mixture of a) a compound of the formula in which R is a benzothiazolyl radical, one which is optionally substituted with identical or different, one or more substituents from the group consisting of halogen, haloalkyl, cycloalkyl, haloalkoxy, alkoxy, alkyl, alkylcarbamoyloxy, arylcarbamoyloxy, alkenylcarbamoyloxy, alkynylcarbamoyloxy, halophenoxy, alkoxyphenoxy, methoxylcarboxy; a cycloalkyl or bicycioalkyl radical, an alkyl radical which is optionally substituted by hydroxy or halogen, R ^ is hydrogen, methyl, benzoyl, cycloalkenyl or an acetyloxymethyl radical, R _{2 is} hydrogen, alkyl, alkenyl, alkynyl, methoxy, an alkyl radical which is optionally substituted by hydroxy or halogen; a carboxymethoxy or alkylcyclohexyl radical, Rz denotes a methyl, ethyl or ethyleneoxy radical,
with b) a compound of the formula X
RCCOR ₁ , «Ti 1
X 0 in which R is halogen, alkyl, haloalkyl, X is halogen, R ₁ is hydrogen, their salts, and R _{1 is} also a. Denotes alkyl, haloalkyl and benzyl radical,
and or c) 2,6-dichlorobenzonitrile. Badische Anilin- & Soda-Fabrik AG 409845/1035