DE2351553A1 - (Non)selective synergistic herbicide - contg. two or more of triazine; benzothiadiazinone dioxide, benzonitrile, phenoxy - carboxylic acid, dinitrophenol, benzaldoxime aryl ether - Google Patents

Abstract

Herbicide contg. a mixt. of the following cpds. is new:- where X = Cl, Br, CN, MeO, OH, azido, thiomethyl, thioethyl, R1, R2 = H, 1-7C alkyl or alkenyl or alkynyl (opt. substd. by CN, OH, Hal, alkoxy) cycloalkyl, acyl. Y = mercapto, NH2, or gps. as for R1, R2 and/or (b) where R = lower alkyl; R1 = H (and its salts); and/or (c) where X = Cl, Br; R = acetyl, octanoyloxy, H (and its salts); and/or (d) where X = Cl, Me, n = 0-3; R = H, alkyl; m = 0-2,R1 = alkyl, H (and its salts); and/or (e) where X = lower alkyl, alkoxy-alkyl, Y =H, lower alkyl, Z = H, alkyl, R = acetyl, halogen acetyl, H; and/or (f) where X = CN, Z = H, Cl, No2, n = 0-3; Y = Hal, alkyl, acetyl, halogen acetyl, H (and its salts); and/or (g) where X = Br, I; R = acetyl, halogenacetyl, H (and its salts); and/or (h) where R = lower alkyl, acetyl, halogenacetyl, phenyl (may be substd. by NO2, CF3) CO-O Alkyl, H (or their salts).

Description

in which X is chlorine, bromine, cyano, methoxy, thiomethyl, hydroxy, thioethyl, azido, R ₁ and R are identical or different and are hydrogen, a straight or branched alkyl, alkenyl or branched alkyl, alkenyl or substituted by cyano, hydroxy, halogen or alkoxy Alkynyl radical with up to 7 carbon atoms, cycloalkyl, acyl, Y has the same meaning as R and R ₁ and Y also denotes alkyl, mercapto or amino and / or

b) a compound of the formula

in which R is lower alkyl, R _{1 is} hydrogen and its salts ^429/75 5098 17/1129 ~ ² ~

- 2 -. 0.1, 30 142

and or

c) a compound of the formula

in which X is chlorine, bromine, R is acetyl, octanoyloxy, hydrogen and its salts

and or

d) a compound of the formula

R f Vo-GH- (CH ₂ ) _m -GOOR ₁

in the X same or different groups of chlorine, Methyl, η 0 to 3, R denotes hydrogen, alkyl, m 0 to 2, R denotes alkyl, hydrogen and its salts,

and or

e) a compound of the formula

in which X is lower alkyl, alkoxyalkyl, Y is hydrogen, lower alkyl, Z is hydrogen, alkyl, R is acetyl, haloacetyl, Means hydrogen and its salts

and or
f) a compound of the formula

> -0-N = CH- / ^) - OR X _n '~ Y

509817/1129

- 3 - O. Zο 30 142

in which X is cyano, Z is hydrogen, chlorine, nitro, η 0 "to 3, Y is halogen, R is alkyl, acetyl, haloacetyl, hydrogen and its salts

and or

g) a compound of the formula

in which X is bromine, iodine, R is acetyl, haloacetyl, hydrogen and its salts means

and or

h) a compound of the formula

OR Cl

KJ ^ ₁ ⁿ -nA _

in which R is a lower alkyl, acetyl, haloacetyl, one which is optionally substituted by nitro or trifluoromethyl Phenyl radical, -C-O-alkyl hydrogen or its

^N I!

Salts means 0
has a better herbicidal effect than the individual active ingredients.

The mixtures can contain one or more compounds of the formulas a to h.

The mixing ratios can be chosen as desired. The mixing ratio of the active ingredients a to b to h is 0.1 up to 10 parts by weight of a to 1 part by weight of b to h, preferably 0.3 to 3 parts by weight of a to 1 part by weight of b to h.

The agents according to the invention can vary in the amount used. The amount used mainly depends on the The type of effect you want. The application rate is in

509817/1129 ⁴ "

- 4 - O.Z. ? 0 142

generally between 0.1 and 30 or more, preferably 0.2 to 6 kg of active ingredients per hectare. The agents according to the invention can be used, among other things, in the pre-planting, post-planting, pre-sowing, pre-emergence, post-emergence processes or while the cultivated plants are in bloom or unwanted plants are applied one or more times.

The mixtures are suitable for use in useful plants, e.g. Triticum spp., Hordeum vulgar, Seeale cereale, Soja hispida, Solanum tuberosum, Saccharum offinarum, Zea mays, Vitis vinifera, Oryza sativa, Pisum sativum, Phaseolus spp., Nicotiana tabacura, Gossypium hirsutum, Ananas spp., Daucus carota, Tilia spp., Alnus spp. to "fight unwanted plants."

In addition, the mixtures can be used as a total agent in trenches, waterways, Track systems, on bare areas, wasteland etc. are used.

The application takes place e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, Oil dispersions, pastes, dusts, grit, granulates by spraying, misting, dusting, scattering or pouring. 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.

Medium-sized mineral oil fractions are used for the production of directly sprayable solutions, emulsions, pastes and oil dispersions to a high boiling point, such as kerosene or diesel oil, also coal tar oils etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, for example methanol, ethanol, propanol, butanol, chloroform, Carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone etc., strongly polar solvents such as dimethylformamide, Dimethyl sulfoxide, N-methylpyrrolidone, water, etc. in • Consider.

509817/1129

- 5 - O.Z. 30 ■ 142

Aqueous application forms can be made from emulsion concentrates, Pastes or wettable powders (wettable powders), oil dispersions can be prepared by adding water. For production of Emulsions, pastes or oil dispersions can use the substances as such or dissolved in an oil or solvent Wetting agents, adhesives, dispersants or emulsifiers are homogenized in water. But it can also consist of active substances, Wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil existing concentrates are produced that are suitable for dilution with water *

The following surface-active substances should be mentioned:

Alkali, alkaline earth, ammonium salts of lignin sulfonic acid, naphthalene sulfonic acids, Phenolsulfonic acids, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, alkali and alkaline earth salts of the Dibutylnaphthalene sulfonic acid, lauryl ether sulfate, petalcohol sulfate, Fatty acid alkali and alkaline earth salts, salts of sulfated hexadecanols, heptadecanols, octadecanols, salts of sulfated Fatty alcohol glycol ethers, sulfonated condensation products Naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, Ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, 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, grit and dust can be mixed or mixed together Milling of the active substances with a solid carrier.

Granules, e.g. coating, impregnation and homogeneous granules, can be produced by binding the active ingredients to solid carriers. Solid carriers are e.g. mineral earth

509817/1129 ⁶ '

- 6 - O.Z. 3C 142

like silica gel, silicas, 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 ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable Products such as grain flour, tree bark, wood and luss shell flour, Cellulose powder and other solid carriers.

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, antifoam agents (e.g. silicone), growth regulators, antidotes or other herbicidal agents effective compounds, e.g.

substituted anilines

substituted aryloxycarboxylic acids and their salts, esters and amides

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 carbamoylalkyl thiol or dithiophosphates substituted quinazolines

substituted Cycloalkylamidocarbonthiolsäuren and their Salts, esters and amides

509817/1129 ~ ⁷ ~

- 7 - 0.2. J

substituted cycloalicylcarbonamidothiazoles substituted dicarboxylic acids and salts, esters and amides substituted dihydrobenzofuranylsulfonates substituted disulfides
substituted dipyridylium salts
substituted dithiooarbamates

substituted dithiophosphoric acids and their salts, esters and amides

substituted ureas substituted hexahydro-1-H-carbothioate 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 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 alkyloarboxylic acids and their salts, esters and amides.

substituted pyrazolium salts substituted pyrazolium allryl sulfates substituted pyridazines

509817/1129 " ⁸ "

- 8 - OZ 30 142

substituted pyridazones

substituted pyridinearboxylic acids and their salts, esters and Amides

substituted pyridines

substituted pyridine carboxylates

substituted pyridinones

substituted pyrimidines

substituted pyrimidones

substituted pyrrolidinoarboxylic acid 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 diones

substituted tetrahydromettianoindenes

substituted tetrab.ydro-diazol-th.iones

substituted tetrab.ydro-tb.iadiazine-tb.ione

substituted tetrahydro-thladiazoldiones

substituted aromatic thiocarboxamides

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 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 according to the invention or mixtures can be used.

The admixture of these agents to the herbicides according to the invention

509817/1129 ~ ⁹

- 9 - "0.?.? 0 142

can be done in a weight ratio of 1:10 to 10: 1. "The same applies to oils, fungicides, nematocides, insecticides, bactericides, antidotes and growth regulators.

The agents have a strong herbicidal effect and can can therefore be used as weed killers or to combat unwanted vegetation. Whether the means act as total or selective agents depends mainly on the amount of active ingredient per unit area.

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

For example, with the agents according to the invention

Gramineae, how

Cynodon spp. Digitaria spp. Echinochloa spp. Setaria spp. Panicum spp. Alopecurus spp. Lolium spp. Sorghum spp. Agropyron spp. Phalaris spp. Apera spp.

Oyperaceae, like

Garex spp. Gyperus spp. Scirpus spp.

dicot weeds such as Malvaceae e.g.

+) Phragmites communis

Dactylis spp. Avena spp. Bromus spp. Uniola spp. Poa spp.
Leptochloa spp, Brachiaria spp, Eleusine spp. Cenchrus spp. , Eragrostis spp, and others

Eleocharis spp, and others

5098 17/1129

- 10 -

Abutilon theoprasti Sida spp, Malva spp.

Compostiae, like

Ambrosia spp. Laotuca spp. Senecio spp. Sonchus app. Xanthium spp. Iva spp. Galinsoga spp. Taraxacum spp. Chrysanthemum spp. Bidens spp. Cirsium spp.

Convolvulaceae, like

Convolvulus spp. Ipomoea spp. Jaquemontia tamnifolia

Cruciferae, like

Barbarea vulgaris Brassioa spp. Capsella spp. Sisymbrium spp. Thlaspi spp. Sinapis arvensis Raphanus spp.

Geraniaoeae, like

Brodium spp. Geranium spp.

.Portulacaoeae such as Portulaca spp.

O. Z. 10 142

Hibiscus spp. and other

Centaurea spp. Tussilago spp. Lapsana communis Tagetes spp. Erigeron spp. Anthemis spp. Matricaria spp. Artemisia spp. and other

Guscuta spp. and other

Arabidopsis thaliana Desourainia spp. Draba spp. Coronopus didymus Lepidium spp. and other

and other

and other

- 11 -

509817/1129

OZ ZO 142

Primulaceae, like. ■

Anagallis arvensis Lysimachia spp.

Rubi'aceae, like

Rictiardia spp. GaIiUm spp.

Scropliulariaceae, such as

Linaria spp. Veronica spp.

Solanaceae »like

Physalis spp. Solanum spp. Datura spp.

Urticaceae such as Urtica spp.

Violaceae such as Viola spp.

Zygophyllaceae such as Tribulus terrestis

Euphorbiaceae such as Mercurialis annua

Umbelliferae, like

Daucus carota Aethusa cynapium

Cominelinaeae

Commelina spp.

and other

Diodia spp. and other

Digitalis spp. and other

Nicandra spp. and other

and other and other Euphorbia spp.

Ammi majus and other

and other

5 0 9 8 17/1129

O.Z. 30 142

Labiatae, like

Lamium spp. Galeopsis spp.

Leguminosae, like

Medicago spp. Trifolium spp. Vicia spp. Lathyrua spp.

Plantaginaceae such as Plantago spp.

Polygonaceae, like

Polygonum spp. Rumex spp.

Aizoaceae, like

Mollugo vertioillata

Amaranthaceaej like Amaranthus spp.

Boraginaceae, like

Amsinolria spp. Myostis spp, Lithospermum spp.

Caryophyllaceae, such as

Stellaria spp. Spergula spp. Saponaria spp. Scleranthus annuus

Glienopoaiaceae, such as Ghenopodium spp. and other

Ses "bania exaltata Cassia spp. And others

and other

Pagopyrum spp. and other

and other

and other

Anohusa spp. and other

Silene © spp. Cerastiwm spp. Aegrostemma githago and others

Atriplex 8pp,

- 13

509817/1128

Kochia 3pp. Salsola potash

Lythraceae such as Cuptiea spp.

Oxalidaoeae such as; Oxalis spp.

Ranunculaoeae, like

Ranunculus spp. Delphinium spp.

Papaveraceae, like

Papaver spp. Pumaria officinalis

Onagraceae such as Jussiaea spp.

Rosaceae, like

Alchemillia spp. Potentilla spp.

Potamogetonaceae such as Potamogeton spp.

Najadaceae such as Najas spp.

Marsileaceae, like

Marsilea quadrifolia

Polypodiaceae such as Pteridium aguilinum

Aliamataceae, like

0.2. 50 U2

Monolepsis nuttalliana and others

and other

Adonis spp. and other

and other

and others and others

and others and others and others

5 0 9 817/1129

-

O. Z. JO 142

and others and others

Alisina spp.

Sagittaria sagittifolia

Equiaetaceae such as Equisetaceae spp.

be harassed.

The connections were made in the greenhouse and in the field

2-chloro-4-allylamino-6 - (/ '- iiiethoxypropyl) amino-1,3,5-triazine 2-chloro-4-allylamino-6-n-propylamino-1,3,5-triazine 2-chloro- 4-allylamino-6-isopropylamino-1,3,5-triazine 2-chloro-4-allylamino-6-ß-methoxyethylamino-1,3,5-triazine Z-chloro-1-isopropylamino-δ-hydroxymethylamino-i, 3 , 5-triazine 2-chloro-4-cyclopropylamino-6-isopropylamino-1,3 »5-triazine 2-chloro-4,6-bis (diethylamino) -1,3,5-triazine 2-chloro-4- iaopropylamino-6-n-propylaniino-1, 3, 5-triazine 2-chloro-4-ethylamino-6-aeli. -butylamino-1,3,5-triazine 2-chloro-4-ethylamino-6-butyn- (1) yl- (3) -amino-1,3 _f 5-triazine 2-chloro-4,6-diethylamino -1,3,5-triazine 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine 2-chloro-4-ethylamino-6-tert-butylamino-1,3,5-triazine 2 -Chlor-4-ethylamino-6-diethylamino-1,3,5-triazine 2-chloro-4-diethylamino-6-isopropylamino-1,3,5-triazine 2-chloro-4,6-diisopropylamino-i, 3 , 5-triazine 2-chloro-4-ethylamino-6- ^ metn.oxypropylamino-1,3,5-triazine 2-chloro-4-isopropylamino-6-methylamino-1,3,5-triazine 2-chloro-4 -isopropylamino-6- ^ methoxypropylamino-1,3,5-triazine 2-chloro-4-ethylamino-6-β- (y ^: methoxy) propylamino-1,3,5-triazine 2- (2-chloro-4 methylamino-1,3,5-triazin-6-yl-amino) -2-metaylpropionitrile

- 15 -

5 0 9 817/1129

- 15 - O. Z. 30 142

2- (2-chloro-4-ethylamino-1,3,5-triazin-6-yl-amino) -2-methylpropionitrile

2-methoxy-4-methylamino-6-isopropylamino-J, 3,5-triazine 2-methoxyH - ätliyiamino-6-tert.-butylamino-1,3,5-triazine 2-meth.oxy-4,6- di (3-methoxypropylaniino) -1, 3, 5-triazine 2-MetTaoxy-4,6- "bis- (ethylaniino) -T, 3,5-triazine 2-methoxy-4-ethylamino-6-sec. -butylaiiiino-1,3,5-triazine 2-methoxy-4-ß-methoxyethylamino-δ-isopropylamino-1,3,5-triazine 2-methoxy-4-ethylamino-6-isopropylalnino-1,3,5-triazine 2-Metb.oxy-4,6-diisopropylamino-1, 3, 5-triazine 2 = methoxy-4-isopylaräino-6-diethylamino-1, 3,5-triazine 2-methoxy-4-inetteylamino-6- sec .- 'butylaniino-1, 3,5-triazine 2-methoxy-4-isopropylamino-6-acetylamino »1, 3,5-triazine, 2-> Metlloxy-4-isopropylamino-6-äthylacetylamino-1,3, 5-triazine 2-methoxy-4 - (/ "- methoxypropyl) aiiiino-6-isoamylamino ~ 1,3,5-triazine 2-metlaylmercapto-4-isopropylaniino-6-seo .- 'butylamino-1, 3,5- triazine

2-MethylmerGapto-4-isopropylamino-6 «tert-butylamino-1,3,5-triazine

2- = methylmercapto-4- (3-nieth.oxy-propyl-ainino) -6-isopropylamine-1,3,5-triazine

2- = methylmercapto-4,6-di- (3mqthoxypropylamino) -1,3,5-triazine 2-methylmercapto-4-methylamino-6 = -isopropylamino «-1,3,5-triazine 2 = methylmercapto-4- ethylamino-6-isopropylamine-1,3> 5-triazine 2-metb.ylmercapto-4-ethylamino-6-sec-butylamino-1,3,5-triazine 2-methylmercapto-4-ethylamino-6-tert . -butylamino-1,3,5-triazine 2-methylmercapto-4,6-diiaopropylamino-1,3,5-triazine 2 = MetliyXthio- = 4-ethylamino-6- € C _t ß, dimethylpropylamino-1,3, 5-triazine 2 ° Mettiylth.io-4-'metb.ylamino-6-n ~ propylamino-1,3,5-triazine

■ '- 16 -509817/1129

- 16 - O.Z.30 142

2-methylthio-4-methylamino-6-sec-butylamino-1,3,5-triazine 2-methylthio-ItM 0-4,6-Ms (/ -me thoxypropylami.no) -1,3,5-triazine 2-methylthio-4-allylamino-6-n-propylamino-1,3,5-triazine 2-methylthio-4-allylamino-6-isopropylamino-1,3> 5-triazine 2-methylthio-4,6-bis ( allylamino) -1,3,5-triazine 2-methylthio-4-amino-6-i3opropylamino-1,3,5-triazine 2-methylthio-4-amino-6-n-propylamino-1,3,5-triazine 2-methylthio-4-diethylaπlino-6-isopropylamino-1,3,5-triazine 2-methylthio-4-äthylaIIlino-6-IIιethylthio-1,3,5-triazine 2-methylthio-4,6-bis (ethylamino) -1,3,5-triazine 2-methylthio-4-ethylamino-6n-propylamino-1,3,5-triazine 2-methylthio-4-ethylamino-6 _< ^ -methoxypropylamino-1, 3, 5-triazine 2- (2-methylthio-4-isopropylamino-1,3,5-triazine-6yl-amino) 2-methylpropiontiitrile

2- (2-methylthio-4-ethylamino-1,3,5-triazine-6yl-amino) -2-methylpropiononitrile

2- (2-Methylth.io-4-methylamino-1, 3, 5-triazine-6yl-amino) -2-methylpropiononitrile

2-ethylthio-4-ethylamino-6-isopropylamino-1,3 _s 5-triazine 2-ethylthio-4,6-Ms- (isopropylamino) -1,3,5-triazine 2-ethylthio-4,6-bis- (ethylamino) -1,3,5-triazine 2-azido-4-ethylamino-6-selc. -tylamino-1,3,5-triazine 2-azido-4-se ■ k ■ ₍ , -l3utylamino-6-methylmercapto-1 _l , 3 j 5-triazine 2-azido-4-ethylamino-6-tert. -t »u tylamino-1,3 ₅ 5-triazine 2-azido-4-isopropylamino» 6-methylmβrcapto-1,3,5-triazine 2-Gyan- "4-ethylamino-6-isopropylamino-1,3,5 -triazine 2-hydroxy-4-amino-6-ethylamino-1,3,5-triazine 2-hydroxy-4-amino-6-isopropylamino- »1,3,5-triazine

- 17 - 509817/1129

- 17 - CS. 30 142

3-isopropyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide

"" -Sodium salt

"" Dimethylamine salt

"" Diethanolamine salt

". ■■■" -Methylamine Salt

¹¹ "'trimethylamine salt

"" Ethylamine salt

"" Diethylamine salt

".11 Ethanolamine Salt

"." Aniline salt

¹¹ "pyridine salt

"" -Phenylenediamine salt

"" -Cyclohexylamine salt

Dodeoyl hexamethylene imine salt

"■" hydrazine salt

"" -Magnesium Salt

¹¹ "calcium salt

"" Ammonium salt

"" Potassium salt

"" Lithium salt

3-isotyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide

"" -Sodium salt

"II - dimethylamine salt

"" Diethanolamine salt

3-sec-butyl-2,1,3-benzothiadiazinon «(4) -2 _? 2-dioxide

"11 sodium salt

»11 -dimethylamine salt

»11 -diethanolamine salt

■ - 18 - 509817/1129

- 18 - O.Z. j> ö 1 ^ 2

3-n -Butyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide

"" -Sodium salt

"" Dimethylamine salt

"" Diethanolamine salt

■ 3-n-Propyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide

"" -Sodium salt

"" Dimethylamine salt

"" Diethanolamine salt

3-ethyl-2,1,3-benzothiadiazinon- (4) -2, 2-dioxide

¹¹ "sodium salt

"" Dimethylamine salt

"" Diethanolamine salt

3-methyl-2, 1,3-t> enzothiadiazinon- (4) -2, 2-dioxide

"" -Sodium salt

"" Dimethylamine salt

¹¹ "diethanolamine salt

3-Isopropyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide-phenylhydrazine salt

3-Isopropyl-2,1,3-t> enzothiadiazinon- (4j_ "" ² > 2-dioxide-β - ("butyl) butoxyhexylamine salt

3 -! - 13Opropyl-2,1 _} 3 ^ tienzothiadiazinon- (4) -2,2-dioxide-hexylamine salt

3-isopropyl-2,1,3 "benzothiadiazinon- (4) -2, 2-dioxide Stearylaminsalz

3-Isopropy1-2,1,3-benzothiadiazinon- (4) -2,2-dioxide-N-methyl-N-butylpiperidine salt

3-Isopropyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide-N-N-dimethylpyridine salt

3-Isopropyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide-ß-ethylhexylamine salt

- 19 5098 17/1129

- 19 - OZ 30 '42

3-Isopropyl-2,1,3-13en.zothiadiazinon- (4) -2,2-dioxide - ^ - isopropoxypropylamine salt . ·

3,5-di; iodine ~ 4-hydroxy-benzonitrile "" "" Sodium Salt

»". ". "Potassium salt

"" "" Lithium salt

"" "" -Methylamine Salt

"" "" Diethanolamine salt

3,5-Diiodo-4-acetyloxy-benzonitrile 3, S-Diood ^ -octanoyloxy-benzonitrile 3,5-Dibroni-4-octanoyloxy-benzonitrile 3,5-Dibromo-4'-acetyloxy-'benzonitrile 3 f 5-I ) i "bromo-4-hydroxy-" benzonitrile

-Sodium salt -potassium salt -lithium salt -dimethylamine salt -Diethanolamine salt

2-sec-butyl-4,6-dinitrophenyl acetate 2 «=> tert-butyl-4,6-dinitrophenyl acetate 2-isopropyl-3-methyl-4j6-dinitrophenol 2-ethoxymethyl-4,6-dinitrophenol 2 sec-amyl-496-dinitrophenol 2- (1-Methylbutyl-) - 4v 6 ~ dinitrophenol sodium 2-sec-butyl-4,6-dinitrophenol "" "" "" -Sodium

2-tert-butyl - = - 5-methyl-4j6-dinitrophenyl acetate 14 _y 6-dinitrophenol

- 20 5 09817/1129

- 20 - 0.3. 30 U2

2-methyl-4,6-dinitrop'h.enol sodium

2-tert-butyl-4,6-dinitrophenol

H ti it ti ti -sodium

3,5-Diiodo-4-hydrox, γ-benzaldoxime-0- (2 'cyano-4'-nitrophenyl) -ather-3,5-Diiodo-4-hydroxy-benzaldoxime-0- (2' cyano-4 ^t -nitrophenyl) -ether-Na.-Salz-

3,5-dibromo-4-hydroxy-benzaldoxime-0- (2'cyan-4'-nitrophenyl) -ether-3,5-dibromo-4-hydroxy-benzaldoxime-O- (2 * cyano-4 '-nitrophenyl) ether-Na.-Salz-

3,5-dibromo-4-hydroxy-benzaldoxime-0- (2 ', 4'-dinitroph.enyl) -ether-

3,5-dibromo-4-b.ydroxy-benzaldoxime-O- (2 ^f , 4 '-dini.tropta.enyl) -ether-Na.-salt-

3-Ph.enyl-4-b.ydroxy-6-cta.loropyridazine 3-phenyl-4,6-dichloro-5-hydroxy-pyridazine [-3-Ph.enyl-6-chloro-pyridazinyl- (4) -I-n -pentyl carbonate 3-Isopropyl-2,1,3-benzoth.iadiazinon- (4) -2,2-dioxide-Zn salt

"" '"-Fe salt

3-tert-Buty1-2,1,3-benzothiadiazinon- (4) -2,2-dioxide

it - ι · ti -Na-salt

"" "-Dimethyl-

aminsaiz

"'" "-Diethanol

amine salt

2- (2-Methyl-4-chloropaenoxy) propionic acid, sodium salt

-Dimethylamine salt

- Diethanolamine salt

-Potassium salt

2- (2 _? 4-Diohlophenoxy) propionic acid sodium salt

-Dimethylamine salt

- 21 9817/1129

- 21 - O.Z, 30 142

2- (2,4-dichlorophenoxy) propionic acid diethanolainine salt

isooctyl ester 2- (2,4,5-irichlorophenoxy) propionic acid potassium salt

-Diethylamine salt - -Dimethylamine salt

- Diethanolamine salt

2- (2,4,5-Trichlorophenoxy) propionic acid isooctyl ester "" "" amyl ester

2- (2-Gtilorphenoxy) -propionic acid-dimethylaniin3-salt 2- (4-chloroplienoxy) propionic acid diethylamine salt 2-chlorophenoxyes3ig3 acid dimethylamine salt 4-chloro-enoxyacetic acid dimethylamine salt 2,4,5-Triohlophenoxyacetic acid potassium salt

-Dietliylamine salt -Dimethylamine salt -diethanolamine salt isooctyl ester amyl ester 2,4-dichlorophenoxy-acetic acid sodium salt

-Dimethylamine salt Diethanolamine salt isooctyl ester 2-methyl-4-chlorophenoxyacetic acid sodium salt

-Dimethylamine salt -diethanolamine salt isooctyl ester

^ - (2-Methyl-4-chlorophenoxy) -butyric acid dimethylamine salt

¹ -diethanolamine salt

509817/1129

- 22 - 0.15. "50 142

> ^ - (2-Methyl-4-chlorophenoxy) butyric acid, sodium salt

-isooctyl ester> ^ (2,4-I> chlorophenoxy) butyric acid, sodium salt

-Dimethylamine salt Diethanolamine salt isooctyl ester

^ - (2-Chlorophenoxy) butyric acid dimethylamine salt ^ (2,4,5-Triohlophenoxy) - "butyric acid-diinethylamine 3-salt ÖC- (2-Metb.ylphenoxy) propionic acid diinethylamine salt <X- (2-methylphenoxy) propionic acid sodium salt <X - (- 2-methylphenoxy) propionic acid isooctyl ester ^^ - (4-Gh.lorophenoxy) -butyric acid - (2,4-dichlorophenoxy) butyric acid potassium salt

tested in a mixture with one another on the plants mentioned in the following examples. They showed appropriate biological Effects like the mixtures mentioned in the examples.

example 1

In the Preiiand different plants were grown at one height from 2 to 26 cm treated with the following individual active ingredients and their mixtures as an emulsion-dispersion-tank mix:

I 3-Isopropyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide

II -sodium salt

III -dimethylamine salt IY -methanolamine salt V 3,5-diiodo-4-hydroxy-benzonitrile salt

71 S-chloro ^ -äthylamino-ö -isopropylamino-i, 3,5-triazine

YII 2- (2-chloro-4-methylamino-1,3,5-triazin-6-yl-amino) -2-methyl-propionitrile

- 23 -

509817/1129

- 23 - ■ 0.25. 30 142

VIII 2-chloro-4,6-di (ethylamino) -1,3,5-triazine

IX 2-chloro-4-ethylamino-6-tert-butylamino-1,3,5-triazine

X 2- (2-chloro-4-ethylamino-1,3,5-triazin-6-yl-amino) -2- - methyl propionitrile

XI 2-methylmercapto-4-ethylamino-6-tert-butylaniino-1,3,5-triazine

XII 2-methylmercapto-4,6-di (i3opropylamino) -1,3,5-triazine

XIII 2-methylmercapto-4-isopropylamino-6 - (^ methoxypropylamino ) -1, 3 »5-triazine

XIY 2-Azido-4-ethylamino-6-tert .- "butylamino-1,3,5-triazine

XV 2-chloro-4-isopropylamino-6-cyclopropylamino-1,3,5-triazine

XVI 2-Methylthio-4-etn.ylamino-δ-cXr-ß-dimeth.ylpropylamine-1,3,5-triazine

with 0.25, 0.5, 1 »1.5 kg / ha a.S.

I + V + VI, I + V + XI, II + V + IX, II + V + X, II + V + XIV,

II + V + XV, II + V + XVI ₉ III + V + VIII, III + V + XII, IV + V + VII, IV + V + XIII ■

with 0.25 + 0.25 + 0.5, 0.25 + 0.5 +0.25, 0.5 + 0.25 + 0.25, 0.25 + 0.25 + 1, 0.25 + 1 + 0.25, 1 + 0.25 + 0.25 kg / ha a.S.

To. 8 "to H days it was found that the mixtures had a Oessere compatibility with the cultivated plants and a "better shows herbicidal action as the individual active substances.

The test result can be seen from the table below.

- 24 509817/1129

O.Z. 30th

Active ingredient I. 1 1.5 II 0.25 0.5 1 1.5 0.25 III 1 1.5 IV 0.25 0.5 1 1.5 V 0.25 0.5 1 1.5 lrg / ha a.S. 0.25 0.5 0.5 Useful plants: 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Hordeum vulgar 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sea cereal 0 0 0 unwanted plants: 10 15th 0 0 12th 15th 0 12th 16 0 10 12th 15th 0 0 5 10 Alopecurus myosuroides 3 5 5 10 0 5 12th 15th 0 10 8th 13th 0 5 10 15th 0 0 8th 15th Poa Annua 0 0 60 75 15th 30th 60 75 20th 5 50 60 25th 35 65 80 15th 20th 30th 40 Salium aparine 15 30th 25th 40 5 10 25th 40 5 30th 40 45 6th 10 35 50 20th 30th 40 45 Lamium amplexxcaule 5 10 10

= no damage = total damage

O.Z.

cn o co

Host VI 1 1.5 VII 0.25 0.5 1 1.5 VIII 0.25 0.5 1 1.5 0.25 13th 1 1.5 X 0.25 0.5 1 1.5 kg / ha a.S. 0.25 0.5 0.5 Useful plants: 0 20th 0 0 0 0 0 0 0 20th 0 15th 20th 0 5 10 15th Triticum aestivum 0 0 5 23 0 0 0 0 0 0 5 22nd 0 10 10 15th 5 10 15th 20th Hordeum vulgar 0 0 10 26th 0 0 0 0 0 0 10 25th 0 5 13th 18th 4th 10 15th 19th Secale cereale 0 0 10 unwanted plants: 87 92 40 50 75 85 40 55 70 80 40 55 65 30th 40 55 65 Alopecurus myosuroides 45 55 90 100 15th 30th 45 60 45 55 75 90 25th 45 40 50 17th 31 50 70 Poa annua 50 65 60 80 15th 30th 55 75 0 10 20th 30th 15th 30th 27 35 5 20th 35 50 G-alium aparine 25 40 50 65 10 30th 45 55 20th 35 50 60 15th 23 50 62 50 65 80 85 Lamium amplexieaule 20 40 35

0 = no damage 100 = total damage

cn cn CO

O.Z.30

Active ingredient X] [ 1 1.5 0.25 XIl 1 1.5 XIII 0.25 0.5 1 1.5 0.25 XI ^- V 1 1.5 0.25 X ¹ ? r 1 1.5 kg / ha a.S. 0.25 0.5 0.5 0.5 0.5 Useful plants: 0 0 0 10 14th 0 0 0 5 0 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 0 10 15th 0 0 0 5 0 0 0 0 0 0 0 0 Hordeum vulgar 0 0 0 0 0 0 6th 10 0 0 0 6th 0 0 0 0 0 0 0 0 Secale cereale 0 0 0 0 0 unwanted plants: 88 84 25th 60 75 44 55 78 90 25th 77 90 40 85 93 Alopecurus myosuroides 45 55 40 50 10 45 55 70 18th 35 50 65 35 45 80 95 20th 55 75 90 Poa annua 30 35 62 81 20th 45 57 70 20th 35 60 77 10 43 35 60 25th 45 60 80 Galium aparine 26 40 53 70 30th 42 65 80 15th 32 50 65 46 20th 80 95 10 45 40 57 Lamium amplexicaule 22 41 55 70 25th

0 = no damage 100 = total damage

cn cn co

O.Z. JO

cn ο co oo

Active ingredient XVI 1 1.5 0.25
0.25
0.5 ] 0.25
0.5
0.25 C + V + VI 0.25
1
0.25 1
0.25
0.25 0.25
0.25
0.5 0.25
0.5
0.25 r + v + XI 0.25
1
0.25 1
0.25
0.25 0.25
0.25
0.5 II + V + 0.5
0.25
0.25 IX 0.25
1
0.25 1
0.25
0.25 kg / ha a.S. 0.25 0.5 0.5
0.25
0.25 0.25
0.25
1 0.5
0.25
0.25 0.25
0.25
1 0.25
0.5
0.25 0.25
0.25 Useful plants: 0 0 0 0 0 0 0 0 0 0 10 0 0 0 Triticum aestivum. 0. 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 15th 0 0 Hordeum vulgar 0 0 • 0 0 0 0 0 5 0 0 0 0 0 ο 0 0 10 0 0 10 0 0 Sea cereal 0 0 0 10 0 0 0 13th unwanted plants: ' 77 92 92 83 90 91 94 83 90 91 80 77 81 88 Alopecurus myosuroides 20 50 80 90 100 86 86 100 93 96 70 66 88 100 73 71 66 76 67 90 70 73 ' Poa annua 25 50 35 58 100 97 87 100 100 100 100 100 67 76 100 100 90 60 97 77 90 100 Salium apärine 15 24 82 95 100 91 100 100 100 100 100 92 100 100 100 100 97 87 80 92 97 98 Lamiujn anrplexicaule 60 68 87 100 88 100 86 100

0 = no damage 100 = total damage

cn cn co

O.Z. jo 142

Active ingredient

II + V + X II + V + XIV

II + V + XV

kg / ha a.S.

0.25 0.25 0.5

0.25

0.5

0.25

0.5

0.25

0.25

0.25 0.25 1

0.25
1

0.25

0.25 0.25

0.25 0.25 0.5

0.25
0.5

0.25

0.5

0.25

0.25

, 5
0.25
1

0.25
1

0.25

0.25
0.25

0.25
0.25
0.5

0.25

0.5

0.25

0.5

0.25

0.25

0.25
0.25
1

0.25

0.25

οι
ο
co

Useful plants:

Triticum aestivum 5

Hordeum vulgar 10

Secale ce real 10

**** unwanted plants:

J ₀ Alopecurus myosuroides 76

to Poa annua 68

(Jalium aparine 87

Lamium amplexicaule 100

5 4

67

52

77

100

5 4

66

58

86

100

10

15 15

90

86

100

100

5 4

100

100

0
0
0

68

80

81

100

0
0
0

71

76

90

100

0
0
0

100

100

98

100

0
0
0

86

89

91

100

0
0
0

83

92

100

100

0
0
0

90

81

100

86

0
0
0

86
76
97
81

0
0
0

77

70

100

76

0
0
0

100
100
100
100

0
0
0

81

83

100

91

0 = without damage
100 = total damage ^

cn cn CO

O.Z. 50

cn
ο
co

Active ingredient 0
0
0 , 25
, 25
, 5 II + V 0.5
0.25
0.25 + XVI 0
0 , 25
, 25 0
0 1
, 25
, 25 0.25
0.25
0.5 0
0
0 III 0
0
0 + V + VIII 0.25
1
0.25 0
0 1
, 25
, 25 0
0
0 , 25
, 25
, 5 0
0
0 III + V 0.5
0.25
0.25 + XI] 0.25
1
0.25 1
0.25
0.25 kg / ha a.S. 0.25
0.5
0.25 0.25
0.25
1 , 25-
, 5
, 25 , 5
, 25
, 25 0
0 , 25
, 25 , 25
, 5
, 25 0.25
0.25
1 Useful plants: 0 0 0 0 0 0 0 0 0 0 0 Triticum aeativum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 Hordeum vulgar 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 10 0 0 Seeale cereale 0 0 0 0 10 0 6th unwanted plants: 87 67 81 38 91 81 88 81 70 77 83 Alopecurus myosuroides 87 76 87 100 86 92 90 76 86 1 00 90 89 80 61 56 98 73 84 Poa annua 90 81 97 100 98 · 1 00 81 81 87 1 00 87 1 00 1 00 54 100 90 100 100 G-alium aparine 1 00 87 100 100 1 00 1 00 97 77 80 91 100 1 00 1 00 1 97 98 100 100 100 Lamium amplexicaule 100 100 91 86 1 00 00 100

= without damage
= total damage

O.Z. 30th

cn ο co 00

Active ingredient ooo IAlA
CM CM LA IV I oool + V + VII O O
ro ro
UI ul 1
0.25
0.25 I ooo ui ro ro
UiUi Γοοο I IV + V LAlA
IA CvJ CM
O * O ~ O * + XIII 0
0 , 25
1
, 25 OO
ro ro
UlUl kg / ha a.S. 0.25
0.5
0.25 LAlA
IACM CM 0.25
0.25
1 , , 25
, 5
, 25 0
0 LALA
OJ CM Useful plants: 0 0 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 Hordeum vulgar 0 0 0 0 0 0 0 0 0 0 0 0 Seeale cereale 0 0 0 0 0 unwanted plants: 86 80 89 91 90 84 92 Alopecurus myosuroides 68 77 87 100 60 62 71 80 60 1 00 63 64 Poa annua 1 00 52 1 57 81 100 100 1 00 1 55 100 86 1 00 100 Galium aparine 93 98 00 100 92 100 93 00 80 1 00 98 70 Lamium amplexicaule 82 86 100 87 1 00

0 = no damage 100 = total damage

K) co cn

cn cn CO

- 31 - O.Z-. 50

. · ■ Example 2

In the open ground, different plants were grown at one height from 2 to 24 cm with the following individual active ingredients and their Mixtures treated as an emulsion dispersion ".

I 3-5-I) ibromo-4-hydroxy-benzaldoxime - 0 - (? '- oyari-4 ^l -nitrophenyl) ether Ea salt

II 3,5-diiodo-4-hydroxy- "benzonitrile

III 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine

IV 2- (2-chloro-4-methylamino-1,3,5-triazin-6-yl-amino) -2-methyl-pyopionitrile

V 2-chloro-4,6-diethylamino-1,3,5-triazine

VI 2-chloro-4-ethylamino-6-tert-butylamino-1,3,5-triazine

VII 2- (2-chloro-4-ethylamino-1, 3, 5-triazine-6yl-amino) -2-methylpropionitrile

VIII 2-Meth.ylmercapto-4-ethylamino-6-tert-butylamino-1,3,5-triazine

IX 2-methylmercapto-4s6-diisopropylamino-1,3,5-triazine

X 2-methylmercapto-4- (3-methoxy-propyl-amino) -6-isopropylamino-1,3,5-triazine

XI 2-Azido-4-ethylamino ^ 6-tert-butylamino-1,3,5-triazine

XII 2-chloro-4-isopropylamino-6-cyclopropylamino-1,3,5-triazine

XIII 2- (1 ', 2 ^f -dimethyl-propylamino) -4-ethylamino-6-methylthio-1,3,5-triazine

with 0.25, 0.5, 1, 1.5 running g / ha aS ^ ^v

I + II + XI, I + II + XII, I + II + XIII, I + II + VIII, I + Π + IX, I + II + X, I + II + VII, I + 11 +, VI, I + II + V, I + II " + IV, I + II + III "

with 0.25 + 0.25 + 0.5, 0.25 + 0.5 + 0.25, 0.5 + 0.25 + 0.25, 0.25 + 0.25 + 1, 0.25 + 1 + 0.25, 1 + 0.25 + 0.25 kg / ha a.S.

509817/1129

- 32 - 0.2.30 142

To. 8 "to H days it was found that the mixtures shows better tolerance by the crop plants and a better herbicidal action than the individual active ingredients.

The test result can be seen from the following table.

- 33 509817/1129

O.Z. 30 142

cn O CD OO

Active ingredient I. 1 0 1.5 0.25 I] 1 1.5 III 0.25 0.5 1 1.5 IV 0.25 0.5 1 1.5 V 0.25 0.5 1 1.5 kg / ha a.S. 0.25 0.5 0 0.5 Useful plants: 0 0 0 0 0 0 0 0 20th 0 0 0 0 0 0 0 25th Triticum aestivum 0 0 0 0 0 0 0 0 0 5 23 0 0 0 0 0 0 5 25th Hordeum vulgar 0 0 15th 0 0 0 0 0 . 0 0 10 26th 0 0 0 0 0 0 10 25th Secale cereale 0 0 15th 0 unwanted plants: 95 20th 0 5 10 45 55 87 92 40 50 75 85 40 55 70 80 Alöpecurus myosuroides 5 10 95 22nd 0 0 8th 15th 50 65 90 100 15th 30th 45 60 45 55 75 90 Poa annua 5 10 100 15th 0 30th 40 25th 40 60 80 15th 30th 55 75 0 10 20th 30th G-alium aparine 15 25th 100 20th 20th 40 45 20th 40 50 65 10 30th 45 55 20th 35 50 60 Lamium amplexicaule 5 10 30th

= without damage
= total damage

KJ CaJ CTl \

O.Z. 50 142

Active ingredient ■ 71 1 1.5 0.25 VI] 1 Ul VIII 0.25 0.5 1 1.5 0.25 13th ¹ < 1.5 X 0.25 0.5 i 1.5 kg / ha a.S. 0.25 0.5 0.5 0.5 Useful plants: 15th 20th 0 10 15th 0 0 0 0 0 10 H 0 0 0 5 Triticum aestivum 0 10 10 15th 5 5 15th 20th 0 0 0 0 0 0 10 15th 0 0 0 5 Hordeum vulgar O 5 13th 18th 4th 10 15th 19th 0 0 0 0 0 0 6th 10 0 0 0 6th Sea cereal 0 10 10 0 unwanted plants: 55 65 30th 55 65 45 55 88 94 25th 60 75 44 55 78 90 Alopecurus myosuroides 40 45 40 50 17th 40 50 70 30th 35 40 50 10 45 55 70 18th 35 50 65 Poa annua 25 30th 27 35 5 31 35 50 26th 40 62 81 20th 45 57 70 20th 35 60 77 G-alium aparine 15 23 50 62 50 20th 80 85 22nd 41 53 70 30th 42 65 80 15th 32 50 65 Lamium amplexicaule 15 35 65 55

=. without damage
= total damage

O.Z. 30,142

cn O CO OO

Active ingredient X] • 1 1.5 XII 0.25 0.5 1 1.5 0.25 XIII 1 1.5 kg / ha a.S. 0.25 0.5 0.5 Useful plants: 0 0 0 0 0 0 0 0 0 Triticum aestivum O O 0 0 0 0 0 0 0 0 0 0 Hordeum vulgar O O 0 0 0 0 0 0 0 0 0 0 Seoale cereale O O 0 unwanted plants: 77 90 40 55 85 93 20th 77 92 Alopecurus myoauroideg 25 45 80 95 20th 45 75 90 25th 50 80 90 Poa annua 35 43 85 60 25th 45 60 80 15th 50 35 58 Galiuni aparine 10 20th 80 95 10 25th 40 57 60 24 82 95 Lamium amplexicaule 46 70 68

0 = no damage 100 = total damage

ro cn

cn cn co

O.Z. 30 142

Active ingredient ] 0.25
0.5
0.25 ; + Ii [+ III 0.25
1
0.25 1
0.25
0.25 I. 0.25
0.25
0.5 LA LA
CM LACM
o ~ o ~ o " + II + IV 0.25
1
0.25 1
0.25
0.25 0.25
0.25
0.5 LA LA
CM LACM
o ~ o "o ~ [+ II + V 0.25
0.25
1 0.25
1
0.25 1
0.25
0.25 kg / ha aS '0.25
0.25
0.5 0.5
0.25
0.25 0.25
0.25
1 0.5
0.25
0.25 Γ OO
ro ro
VJlVJl 0.5
0.25
0.25 Useful plants: 0 0 o · 0 0 0 Ο ' 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 Hordeum vulgar 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 10 0 0 Sea cereal 0 0 10 0 0 0 unwanted plants: 86 90 98 93 82 87 92 97 82 100 87 92 Alopecurus myoauroides 97 91 91 100 98 100 72 57 88 100 64 66 98 87 87 100 94 98 Poa annua 100 97 97 100 100 100 98 88 62 87 98 100 77 72 92 87 80 100 G-alium aparine 100 90 100 100 100 100 92 81 92 100 91 100 98 91 76 100 100 100 Lamium amplexicaule 100 87 100 77 100 86

= without damage
= total damage

cn cn co

O.Z. 50 142

Host ] 0.25
0.5
0.25 [+ I] C + YI 0.25
1
0.25 1
0.25
0.25 0.25
0.25
0.5 0.25
0.5
0.25 I + II + YII 0.25
0.25
1 0.25
1
0.25 1
0.25
0.25 ooo
Ui ro ro
VJlUi I. + II + YIII 0.25
1
0.25 1
0.25
0.25 tg / ha as 0.25
0.25
0.5 0.5
0.25
0.25 0.25
0.25
1 0.5
0.25
0.25 0.25
0.5
0.25 0.5
0.25
0.25 0.25
0.25
1 Useful plants: 0 0 0 5 0 10 0 - 0 0 0 0 Triticum aestivum 10 0 0 15th 0 0 10 5 0 15th 5 5 0 0 0 0 0 0 Hordeura vulgar 5 0 0 10 0 0 10 4th 5 15th 4th 4th 0 0 0 0 0 0 Seeale cereale 10 0 13th 4th 0 0 0 unwanted plants: 82 86 92 85 75 100 80 85 98 95 98 Alopecurus myosuroides 86 68 87 97 74 76 73 58 80 90 70 78 80 86 92 100 83 85 Poa annua 70 90 72 93 97 100 '96 88 62 100 96 100 100 75 80 85 100 100 G-alium aparine 95 95 98 93 98 100 100 100 97 100 100 100 100 100 100 100 100 100 Lamium amplexicaule 97 90 100 100 96 92 100

= without damage
= total damage

cn cn co

O.Z.

142

Active ingredient

I + II + IX

I + II + X

+ II + XI

kg / ha a.S.

0.25 0.25 0.5

0.25

0.5

0.25

0.5

0.25

0.25

0.25 0.25

0.25 1

0.25

0.25 0.25

0.25
0.25
0.5

0.25

0.5

0.25

0.5

0.25

0.25

0.25 0.25

0.25
1

0.25

0.25
0.25

0.25
0.25
0.5

0.25

0.5

0.25

0.5

0.25

0.25

0.25

0.25

0.25
1

0.25

Useful plants:

Triticum aestivum 0

Hordeum vulgar 0

Secale oereale 0

^u "desirable plants;

κ? Alopecurus myosuroides 90

^<o Poa annua 90

Galium aparine 100

Iamiurn amplexicaule 100

0 0 0

70

55

95

100

0 0 0

75

60

100

100

10

10

100 100 100 100

0 0 0

75

68

98

100

80

72

100

100

0
0
0

97

76

100

0 0 0

86 60

94 88

0
0
0

100

91

100

100

0
0
0

91

67

100

99

0
0
0

95

70

100

100

0
0
0

90

88

94

100

0
0
0

76

82

90

100

0
0
0

78

85

97

100

0
0
0

100
100
100
100

0
0
0

88

90

98

100

0 = no damage 100 = total damage NJ CO Cn

O.Z.

cn C? co

Host I. + II 0 + XII 0.25
1
0.25 1
0.25
0.25 0.25
0.25
0.5 I. + II + XIII 0.25
1
0.25 1
0.25
0.25. "kg / ha as 0.25
0.25
0.5 0.25
0.5
0.25 0.5
0.25
0.25 0 0.25
0.25
1 0.25
0.5
0.25 0.5
0.25
0.25 0.25
0.25
1 Useful plants: - 0 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 O 0 0 0 0 0 Hordeum vulgar 0 • 0 96 0 0 0 0 0 0 0 0 0 Sea cereal 0 0 78 0 0 0 0 unwanted plants: 100 90 96 95 75 95 ' Alopecuru3 myosuroides 97 85 98 100 86 78 95 75 78 100 85 82 Poa annua 96 73 100 100 100 96 80 80 100 100 100 Galium aparine 100 97 100 97 100 100 94 98 100 100 100 Lamium amplexicaule 95 92 100 100 100 100

0 = no damage 100 = total damage

CO cn

cn cn CO

- 40 - O.Z.JO 142

■ Example 3

Various plants were grown in the greenhouse at a height of 1.5 to 23 cm with the following individual active ingredients and their mixtures treated as solution-emulsion-dispersion:

I 3-Isopropyl-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide

II 3-Isopropyl-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide, sodium salt

III 3-Isopropyl-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide-dimethylamine salt

IY 3-Isopropyl-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide-diethanolamine salt

VII 2- (2-chloro-4-methylamino-1,3,5-triazin-6-yl-amino) -2-methylpropionitrile

VIII 2-chloro-4,6-diethylamino-1,3,5-triazine

IX 2-chloro-4-ethylamino-6-tert-butylamino-1,3, 5-triazine

XI 2-methylmercapto-4-ethylamino-6-tert-butylamino-1,3,5-triazine

XII 2-methylmercapto-4j6-diisopropylamino-1,3,5-triazine

XIII 2-methylmercapto-4- (3-methoxy-propyl-amino) -6-isopropylamino-1,3 j5-triazine

XIV 2-Azido-4-ethylamino-6-tert-butylamino-1,3,5-triazine

XV 2-chloro-4-cyclopropylamino-6-isopropylamino-1,3,5-triazine

XVI 2- (2-chloro-4-ethylamino-1,3,5-triazin-6-yl-amino) -2-methyl-propionitrile

XVII 2-sec-butyl-4> 6-dinitro-phenyl acetate

XVIII 2-tert-butyl-4,6-dinitro-phenol sodium salt

XIX 2-methyl-4,6-dinitro-phenol sodium salt

XXII 3 $ 5-dibromo-4-hydroxy-benzaldoxime-0- (2 '-cyan-4 ^f -nit roph.enyl) -äthernat riumsalz

• ■ - 41 -

509817/1129

- 41 - OZ. 30 1 ^L ! 2

XXIII 3,5-I) it) rom-4-hydroxy-'benzaldoxime-0- (2 ', 4'-dinTfropkeriyx) -ätber

XXIY 3-PtLenyl-4-h.ydroxy-6-ch.loropyrid.azine XXY 3-I ⁾ h.enyl-4,6-diochloro-5-tydroxy-pyridazine

XXVI £ -3-Ph.enyl-6-Gh.lor-pyridazinyl- (4) -I-n-pentyl carbonate

XXVII (£ - (2-Methyl-4-one.lor-ph.enoxy) -propionic acid-dimethylamine salt

XXVIII cC- (2,4-dichlorophenoxy) propionic acid dimethylamine salt

XXIX 2,4-Diclilor-pTienoxy-acetic acid-diniethylamine 3 salt

XXX 2-methyl-4-ob.lor-ph.enoxy-e ^ 3igaäurβ-Diπleth.ylaIIlin3alz

XXXI 2,4,5-trichloro-phenoxy-acetic acid isooctyl ester

XXXII oL (2,4,5-trichlorophenoxy) propionic acid potassium salt

XXXIII _< ^ - (2 ₎ 4-DiGhlor-ph, enoxy) - 'butter acid, sodium salt

XXXIV 3,5-di "bromo-4-h, hydroxy-benzonitrile

XXXV 3,5-diiodo-4-h.ydroxy-benzaldoxime-0- (2 ^{l l} Gyan-4 -nitrophenyl) ether

XXXXI oC (2-Meth.yl-4-oh.lor-ph.enoxy) -propionic acid sodium 3 salt XXXXII OC (2,4-dich, lor-p1ienoxy) propionic acid sodium salt XXXXIII 2,4,5 - Trictilor-phenoxy-acetic acid XXXIX 3,5-di "bromo-4-octanoyloxy-benzonitrile

with 0.25, 0.5 and 1 kg / ha a.S.

I + IX + XVIII, II + XVI + XVII, III + XV + XIX, IV + XIV + XX, IV + XIII + XXI, II + VIII + XXII, I + VII + XXIII, III + XI + XXIV, I + XII + XXV, II + XIII + XXVI, XXVII + XXXIV + XVI, XXVIII + XXXIV + XV, XXIX + XXXIV + VIII, XXIV + XXXIV + XII, XVII + XXXXI + VIII, XVIII + XXXXII + XIII, XIX + XXIX + XV, XXII + XXX + XVI, XXIV + XXXXIII + VII, XXII + XVII + XIII, XXX + XXXIV + XIII, XXXI + XXXIV + IX, XXXII + XXXIV + XIV, XXXIII + XXXIV + VII, XVII + XXXIV + XV, XVIII + XXXIV + VIII, XIX + XXXIV + XI, XXXV + XVIII + VIII, XXIV + XIX + XV, XXIV + XXII + VIII, XXIV + -XXIII + XIII

- 42 - 509817/1129

- 42 - O. Zr -50 ί42

with 0.25 + 0.25 + 0.5, 0.25 + 0.5 + 0.25- and 0.5 + 0.25 + each 0.25 kg / ha a.S.

After 10 to 15 days 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.

- 43 509817/1129

O.Z. 30 142

Active ingredient I. 1 0.25 0.5 1 III 0.25 0.5 1 IY 0.25 0.5 1 VII 0.25 0 0.5 1 viii 0.25 0.5 1 IX 0.25 0.5 1 kg / ha as, 0.25 0.5 l 0 Useful plants: 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 15th Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 5 10 Hordeum vulgar 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 10 13th ⁰¹ Seeale cereale 0
O 0 CD 40 CXD 15th "~ * unwanted plants: 10 0 0 12th 0 10 12th 0 10 12th 15th 50 75 40 55 70 40 45 55 ~ j —-————————————————
_ * Alopecurus myosuroides 3 5 5 0 5 12th 0 5 8th 0 5 10 10 30th 45 45 55 75. 25th 30th 40 "- * Poa annua 0 0 50 15th 30th 60 20th 30th 50 25th 35 65 30th 55 0 10 20th 15th 23 27 cd G-alium aparine 15 30th 25th 5 10 25th 5 10 40 6th 10 35 30th 45 20th 33 50 15th 35 50 lamium amplexicaule 5 10

Ο = without damage
= total damage

O.Z. 30th

Active ingredient XI 1 0.25 XIl 1 0.25 XIIl 1 XIY 0.25 0.5 1 XY 0.25 0.5 1 XYI 0.25 0.5 -t XYII 0.25 0.5 1 kg / ha a.S. 0.25 0.5 0.5 0.5 Useful plants: 0 0 10 0 0 0 0 0 0 0 0 0 5 10 0 0 0 Triticum aestivutn 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 5 10 15th 0 0 0 Hordeum vulgar 0 0 0 0 0 6th 0 0 0 0 0 0 0 0 0 4th 10 15th 0 0 ' 0 Seoale cereale 0 0 0 0 unwanted plants: SB 25th 60 44 73 25th 45 77 40 55 85 30th 40 55 0 0 5 Alopecurug myosuroides 45 55 40 10 45 55 18th 55 50 35 43 SO 20th 45 75 17th 31 50 0 0 0 Poa annui 30 35 62 20th 45 57 20th 35 60 10 20th 35 25th 45 60 5 20th 35 18th 30th 40 G-alium aparine 26 40 53 30th 42 65 15th 35 50 46 70 80 10 25th 40 50 65 80 32 50 70 Lamium amplexicaule 22 41 55 32

0 = no damage 100 = total damage

cn cn approx

O.Z. 50 142

αϊ ο co οο

Active ingredient XVIII 1 0.25 XIX 1 0.25 XX 1 0.25 XX] [ 1 0.25 XXI] ■ 1 XXIII 0.25 0.5 1 XXIV 0.25 0.5 1 kg / ha a.S. 0.25 0.5 0.5 0.5 0.5 0.5 Useful plants: 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 TritiauTi aestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Hordeuin vulgar 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Se.cale 'cereale 0 0 0 0 0 0 unwanted plants: 5 0 3 0 0 0 5 5 15th 0 0 0 0 0 0 Alopecurus myosuroici.es 0 3 3 0 0 0 0 0 5 0 0 3 5 10 15th 0 5 10 0 0 0 Poa annua 0 0 58 25th 0 60 15th 0 40 9 0 40 15th 10 95 20th 30th 70 5 10 20th G-alium aparine 20 35 75 30th 35 80 12th 20th 55 15th 25th 62 5 30th 95 25th 35 75 5 11 50 Lamium amplexicaule 25 45 45 30th 30th 10

0 = no damage 100 = total damage

GO cn

cn cn Ca>

O.Z. JO

cn o co

Active ingredient 0.5 r 1 XXVI 0.25 0.5 1 XXYII 0.25 0.5 1 XXYIII 0.25 0.5 1 XXIX 0.25 0.5 1 0.25 XX) ■ 1 0.25 XXX] 1 Tcg / ha a.S. 0.25 0.5 0.5 Useful plants: 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Hordeum vulgar 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Secale cereale 0 0 0 unwanted plants: 5 15th 10 30th 60 0 0 0 0 0 0 0 0 0 0 0 0 0 Alopecurus myosuroides 0 10 20th 15th 40 60 0 0 5 0 0 0 0 0 0 0 0 10 0 0 0 Poa annua 0 20th 40 20th 40 60 15th 30th 50 10 20th 65 5 10 20th 5 5 20th ¹ 15 0 70 Galium aparine 10 17th 30th 10 20th 45 10 15th 25th 15th 25th 60 20th 35 80 20th 10 80 20th 30th 85 Lamium amplexicaule 8 30th 40

0 = no damage 100 = total damage

- co Cn

0.Z.30

σ co οο

Active ingredient XXXII 1 XXXIIl 0.25 0.5 1 0.25 XXXIV 1 XXX? 0.25 0.5 1 XXXXI 3.25 0.5 1 0.25 XXXXII 1 ΊΠΠΓΤΤΤΤ 0.5 1 kg / ha a.S. O "25 0.5 0.5 0 _P 5 0.25 Useful plants: 5. 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 Triticum aeativum 0 0 6th ρ 0 0 0 5 5 0 0 0 0 0 0 0 0 0 0 0 0 Hordeum vulgar 0 0 7th 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 Sea cereal 0 0 0 0 0 unwanted plants: 5 0 0 0 0 12th 0 0 10 0 0 0 0 0 0 5 Alopecurua myosuroides 0 0 5 0 0 0 0 0 15th 0 5 15th 0 0 5 0 0 0 0 0 7th Poa annua 0 3 57 10 12th 18th 5 0 65 15th 35 63 15th 28 50 15th 0 50 0 30th 60 Galium aparine 17 40 80 15th 20th 35 10 20th 50 10 40 75 7th 15th 25th 10 35 45 15th 40 75 Lamium amplexicaule 15 35 30th 15th 18th

0 = no damage 100 = total damage

O.Z. Λ V.2

Cn
CD
CO
OO

Active ingredient XXXIX 0.5 1 I + IX + XVIII 0.25
0.5
0.25 0.5
0.25
0.25 II + XVI + XVII ooo
K) Ul K)
Ul ul ooo
KJKJUI
UlUl III + XV + XIX 0.25
0.5
0.25 0.5
0.25
0.25 IV + XIV + XX ooo
ro ui ro
Ul ul ooo
ro ro ui
UlUI IV + XIII + XXI 0.25
0.5
0.25 0.5
0.25
0.25 II + VIII + XXII 0.25
0.5
0.25 ooo
ro ro ui
UlUl kg / ha a.S. 0.25 0.25
0.25
0.5 0.25
0.25
0.5 0.25
0.25
0.5 0.25
0.25
0.5 0.25
0.25
0.5 0.25
0.25
0.5 Useful plants: 0 0 10 0 5 0 0 0 Ό 0 0 0 0 0 Triticum aestivum O 0 0 0 5 0 0 10 5 0 0 0 0 0 0 0 0 0 0 0 0 Hordeum vulgar 0 0 0 0 10 0 5 10 4th 0 0 0 0 0 0 0 0 0 0 0 0 Secale cereale 0 0 4th 0 0 0 0 unwanted plants: 0 5 ■ 37 84 78 69 94 88 83 78 93 94 98 83 Alopecurus myoauroides' 0 0 5 86 70 65 70 71 62 80 85 76 69 83 84 84 75 63 89 98 95 Poa annua 0 15th 55 65 96 100 58 92 91 75 100 100 84 100 100 60 100 100 94 87 90 Galium aparine 5 25th 47 100 100 90 90 100 100 100 100 92 95 100 100 100 93 81 95 95 80 Lamium amplexicaule 10 100 100 100 100 91 84

= without damage
= total damage

• 4a.-

CO CJl

LO OO CsI

001 001 001 SS S6 68 0OL 0OL 0Ot 08 06 S8 28 L6 06 9L 68 LL £ 8 86 06 ■ θΐηΒοτχθχΰιπΒ πίπτΐπει LS S9 89 68 t6 0OL 08 6L 6L 0OL 0Ot 0Ot 06 0Ot 0Ot 0Ot 001 £ 6 0OL 0Ot 0OL SUTJBdB πητχΒ {) fr8 £ 8 £ 6 S9 L9 £ 8 6S 09 LL 08 S6 0Ot OIL SL 08 SL 2L 89 SS 69 09 BClUtIE BOä 6L QL £ 6 SL QL 26th OIL OIL 8L 06 0Ot 0OL 06 86 06 t6 26th 88 SS 26th 1.8 sspToanso / tn snanosdoxv 0 0 0 O O 0 OIL 0 0 0 0 0 0 0 0 0 0 0 0 0 . 0 O O 0 S. S. Ot 0 0 0 0 0 0 0 0 0 . 0 0 0 θλβΒχΠΑ tanspaoH 0 S. 0 O VJI 0 0 0 S. 0 0 0 0 0 0 0 0 0 0 0 0 mnAx.saB.mnoT.TYes; SZ'O
S2'0
SO S2'0
SO
SS'O SO
SS'O
ss'o S2'0
SS'O
SO OOO
ro vji ro
VJl VJl S'C
S2'C
S2'C j OOO
ro rovji
VJlVJl SS'O
SO
SS'O SO
SS'O
SS'O S2'0
S2'0
SO S2'0
SO
S2'0 OOO
I vji ro ro
I VJlVJl SS'O
S2'0
SO S2'0
SO
S2'0 OOO
vji ro ro
VJIVJl S2'0
S2'0
SO S2'0
SO
S2'0 SO
S2'0
S2'0 S2'0
SS Ό
SO S2'0
SO
SS'O ΙΙΙΛ + ΛΙΧΧΧ + ΛΙΧΧ ΛΧ + ΛΙΧΧΧ + ΙΠΛΧΧ ΙΛΧ + ΛΙΧΧΧ + ΙΙΛΧΧ ΙΛΧΧ + ΙΙΙΧ + ΙΙ ΛΧΧ + ΠΧ + Ι ΛΙΧΧ + ΙΧ + ΙΙΙ so
ss'o
SSΌ 'S'B Bii / SJi ΙΙΙΧΧ + ΙΙΛ + Ι JJop.S3iaTM

OO O) O LO

oi * Z * O

LO LO ν— LO CO CN

S6 OOL OOL 08 ie 26th OOL OOL OOL OOL L6 OOL OOL S6 OOL OOL OOL OOL 26th OOL OOL θχηΒοτχθχαιπΒ ΐπητπίΕΊ OOL OOL OOL 08 Lq 88 S8 08 06 OOL OOL OOL OOL OOL OOL t8 9A L8 S /, 28 06 9uto; bc [b ΐπητχΒί) OIL £ 9 08 S9 S9 L9 L9 99 iL S9 L9 Sg 6S 09 ZL £ 8 t-8 ie 2S SS t / 9 ΒΠαΠΒ BO «! ze 88 86 08 eL LQ 08 28 SL 08 S6 98 28 ie eL 08 ze t9 S9 £ g sspjoanso ^ m δηαηοθαοχν 0 O O 0 0 0 t- t OIL 0 0 0 0 0 0 0 0 O 0 0 0 θχΒΘΛΘΟ θχΒΟθδ 0 O O 0 0 0 VJl S. OIL 0 0 0 0 0 0 0 0 0 0 0 0 θΛΕ§χηΔ nmepjoji 0 O O 0 0 0 0 0 S. 0 0 0 0 O' 0 O 0 0 0 S. 0 tntlATp.SeE EtIOT ^ TJJi S2 | O
"SO S2'0
SO
S2'0 in in
CM CM in
OOO S2'0
S2'0
SO S2'0
SO
S2'0 ooo
ui ro ro
UlUl S2'0
SO S2'0>
SO
S2'0 SO
S2'0
S2'0 ooo
ro ro ui
UlUl S2'0
SO
S2'0 ooo
ui ro ro
uiui in in
in cm cm
ooo S2'0
SO
S2'0 SO
S2'0
S2'0 ooo
ro ro ui
UlUl ooo
ro ui ro
UI ul ooo
ui ro ro
UlUl ooo
ro ro ui
UlUl S2'0
SO
S2'0 ΙΙΙΧ + ΙΙΛΧ + ΙΙΧΧ ΙΙΛ + ΙΙΠΧΧΧ + ΛΙΧΧ ΙΛΧ + ΧΧΧ + ΙΙΧΧ ΛΧ + ΧΙΧΧ + ΧΙΧ rnx + πχχχχ + ΐπΛχ IHA + IXXXX + 1ΙΛΧ SO
S2'0
SZ'O 'S'B Bq / S3i ΙΙΧ + ΛΙΧΧΧ + ΛΙΧΧ jjo ^ sjutk

CXJ OT O LO

2tf L. Oi * Z Ό

- OS -

OOL OOL OOL OOL OOL OOL OOL, OOL OOL 08 te S6 OOL OOL OOL OOL OOL OOL S6 OOL OOL θχΠΒΟΤΧΘχαίΠΒ ΠίηΤΠΙΒΙ OIL OOL OOL 08 6i ti OOL OOL OOL Room t8 £ 8 £ 6 SS Z8 68 88 S8 Si £ 8 28 euxaBclE πΐητχΒ-Q Li Oi Si t8 £ 8 Z6 Room Si £ 8 S9 S9 99 08 LL £ 8 t9 S9 69 Σ9 6S iL BnUUB BOi .se; 06 S6 £ 8 08 £ 6 S8 S8 Z6 6i 08 LQ Oi Si S8 08 08 t8 £ 8 Σ8 26 BspfoaneoJCm snanoadoxv O O O O O O O O O O O O O O O O O OIL O O O O O O O O O O O O O O .0 O O O O S. O O ' O θαβΒχηΔ innspaoH O S. O O S. O O VJl O O S. O O S. O O S. OIL O S. Π TUfIATQ-S ΘΒ mnOTQ.T ^ Lir sz'o
sz'o
SO SZ'Q
SO
SZ'O SO
sz'o
sz'o sz'o
sz'o
SO SZ'O
SO
SZ'O SO
sz'o
SZ Ό sz'o
SZ'O
S ⁴ O sz'o
SO
sz'o SO
sz'o
sz'o SZ'O
sz'o
SO sz'o
SO
sz'o SO
sz'o
sz'o Sz'o
SZ'O
SO sz'o
SO
sz'o SO
SZ'O
SZ'O SZ'O
SZ'O
SO SZ'O
SO
SZ'O SO
SZ'O
SZ'O SZ'O
SZ'O
SO SZ'O
SO
SZ'O • {ΙθΖΐΙΒχΧ 0.23. ti ^] ΙΧ + ΛΪΧΧΧ + ΧΙΧ niA + Aim + imx ΛΧ + ΛΙΧΧΧ + ΙΙΛΧ ΙΙΛ + ΛΠΧΧ + ΙΠΧΧΧ ΛΙΧ + ΛΙΧΧΧ + ΠΧΧΧ ΧΙ + ΛΙΧΧΧ + ΙΧΧΧ SO
sz'o
Sz'o 's * ε b ^ / s ^ i ΙΙΙΧ + ΛΙΧΧΧ + ΧΧΧ JJoq-S ^ aTW

OO CT) O LO

Oi 'Z * 0

- LS -

Active ingredient XXXV + XVIII + VIII 0.25
0.5
0.25 0.5
0.25
0.25 XXIV + XIX + XV 0.25
0.5
0.25 0.5
0.25
0.25 XXIV + XXII + VIII 0.25
0.5
0.25 0.5
0.25
0.25 XXIX + XXIII + XIII 0.25
0.5
0.25 0.5
0.25
0.25 Ά K) kg / ha as 0.25
0.25
0.5 0.25
0.25
0.5 0.25
0.25
0.5 0.25
0.25
0.5 CO
cn Useful plants: 0 0 0 0 0 0 0 0 cn Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 cn _o Hordeum vulgar 0 0 0 0 0 0 0 ■ o 0 0 0 0 ⁰⁰ Seeale cereale 0
CO 0 0 0 - * unwanted plants: 81 80 80 80 90 83 84 83 co Alopecurus myosuroides 93 84 88 94 67 65 97 95 87 93 64 63 Poa annua 95 88 92 88 100 100 98 78 70 75 95 90 G-alium aparine 84 100 100 100 100 92 80 80 80 98 95 91 Lamium amplexicaule 100 100 90 100 O = without damage 100 = total damage

- 53 - O.Z. 30 142

In the greenhouse, various plants were grown in a growth, height from 2 to 22 cm with the following single fabrics and their Mixtures treated as powder or dispersion:

VIII 2-chloro-4,6-diethylamino-1,3,5-triazine

XI 2-methylmercapto-4-ethylamino-6-tert-butylamino-1,3,5-triazine

XIII 2-methylmercapto-4- (3-methoxy-propyl-aniino) -6-isopropylamino-1,3,5-triazine

XVI 2- (2-chloro-4-ethylamino-1,3,5-triazin-6-yl-amino) -2-methyl-propionitrile

XVII 2-sec-butyl-4,6-dinitro-phenyl acetate

XVIII 2-tert-Butyl-4,6-dinLtrophenol sodium salt

XIX 2-methyl-4,6-dinitro-phenol sodium salt

XXII 3,5-Dibromo-4-hydroxy-benzaldoxime-0- (2'-cyano-4-nitrophenyl) ether

XXIV 3-Phenyl-4-hydroxy-6-chloropyridazine

XXVII c ^ .- (2-methyl-4-chlorophenoxy) propionic acid diniethyl

amine salt

XXVIII Ct- (2,4-dichlorophenoxy) propionic acid dimethylaniine salt

XXIX 2 ^ -Dichloro-phenoxy-acetic acid-dimethylamine salt

XXX 2-methyl-4-chlorophenoxy-acetic acid dimethylamine salt

XXXI c ^ - (2,4,5-trichlorophenoxy) propionic acid isoo'k: tyl ester XXXIII Jf- (2,4 -dichlorophenoxy) butyric acid sodium aalt

XXXV 3,5-Diiodo-4-hydroxy-benzaldoxime-0- ( ^2f cyano-4 »-nitrophenyl) -ether

XXXVI 3,5-dibromo-4-hydroxy-benzaldoxime-0- (2'cyan-4 * -nitrophenyl) -ether

XXXVII 3,5-Diiodo-4-hydroxy-benzaldoxime-0- ( ^2f cyano-4'-nitropheny1) -ether-sodium salt

- 54 509817/1 129

- 54 - 0, Z, 30 14?

XXXXIII 2,4,5-trichloro-phenoxy-acetic acid-potassium salt 235 1553 with 0.5, 0.75, 1 and 1.5 kg / ha aS

XXII + VIII, XXXVI + XIII, XXXVII + XVI, XXXV + XI, XXVII + XXII, XXVIII + XXXVI, XXX + XXXVII, XXIX + XXXV, XXXXIII + XXII, XXXI + XXXVI, XXXIII + XXIV, XVII + XXXVI, XIX + XXXVII, XVIII + XXII, XVII + XXIV, XXII + XXIV

with 0.5 +1.1+ 0.5 and 0.75 + 0.75 kg / ha. a.S.

After 9 "to H days 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 result of the experiment can be seen in the table below.

- 55 5 098 17/1 129

O.Z. 30 142

Active ingredient VIII 1 1.5 0.5 0.75 pi 1 1.5 0.5 XVI 1 1.5 0.5 XV [I. 1 • 5 1.5 XVIII 0.5 0.75 1 1.5 lcg / ha a.S. 0.5 0.75 0.75 0.75 0 Useful plants: 0 20th 0 0 0 0 5 10 15th 0 0 40 0 0 0 0 0 Triticüm aestivum 0 0 5 22nd 0 0 0 0 10 7th 15th 20th 0 0 0 70 0 0 0 0 0 Hordeum vulgar 0 0 10 25th 0 0 0 0 10 12th 15th 19th 0 0 0 0 0 0 0 0 Secale cereale 0 0 12th 0 unwanted plants: 70 80 55 70 88 94 40 55 65 0 10 3 5 5 T Alopecurus myosuroides 55 63 75 90 35 37 40 50 31 47 50 70 0 3 0 0 0 3 5 Poa annua 55 68 20th 30th 40 50 62 81 20th 37 35 50 30th 0 50 35 45 58 68 Galium aparine. 10 15th 50 60 41 47 53 70 65 28 80 85 50 35 85 45 55 75 85 Lamium amplexicaule 35 42 75 60

= without damage
= total damage

cn cn to

OZ 30 142

cn ο co

Host XIX 1 1.5 XXII 0.5 0.75 1 1.5 XXIV 0.5 0.75 1 1.5 XXYII 0.5 0.75 1 1.5 XXYIII 0.5 0.75 1 1.5 lcg / ha a.S. 0.5 0.75 Useful plants: 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Hordeum vulgar 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Secale cereale 0 0 unwanted plants: 3 5 10 12th 15th 20th 0 0 0 2 0 0 0 10 0 0 0 3 Alopecurus myosuroidea 0 0 0 0 10 12th 15th 22nd 0 0 0 5 0 0 '5 12th 0 0 0 5 Poa annua 0 0 60 65 30th 65 95 100 10 15th 20th 30th 30th 40 50 70 20th 30th 65 75 Galium aparine 55 50 80 85 10 60 95 100 11 25th 50 70 15th , 20 25th 50 25th 35 60 70 Lamium amplexioaule 45 60

= without damage
= total damage

co cn ^

- ■■>; -

O.Z. "0

cn o co

Active ingredient XXIX 1 1.5 XXX 0.5 0.75 1 1.5 XXXI 0.5 0.75 1 1.5 XXXIII 0.5 0.75 1 1.5 XXXV 0.5 0.75 1 1.5 k-g / ha a.S. 0.5 0.75 Useful plants: 0 Q 0 0 Q 0 0 0 5 10 C. 0 0 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 0 0 0 0 0 7th 10 0 0 0 0 0 0 0 ' 0 Hordeum vulgar 0 .0 0 0 0 0 0 0 r \
O 0 10 12th 0 0 0 0 0 0 0 0 Secale eereale 0 0 unwanted plants: 0 0 0 0 0 0 0 0 0 5 0 0 0 3 0 5 10 15th Alopecurus myosuroides 0 0 0 5 5 7th 10 15th 0 r \ 7th 0 0 0 5 5 10 15th 20th Poa annua 0 0 20th 25th 10 15th 20th 25th 40 48 52 85 12th 15th 18th 25th 35 50 63 80 Galium aparine 5 12th 80 80 70 45 80 82 40 60 35 90 21 30th 36 47 40 60 75 85 Lamium amplexicaule 20 50

sr "Z.

0 = no damage 100 = total damage

CO Cn

Cn cn CO

-5B-

o.ζ.30 u:

Active ingredient XXXVI ι 1.5 XXXYII 0.5 0.75 1 1.5 XXXXIII 0.5 0.75 1 1.5 XXII + VIII 1 0.75 XXXVI + XIII 1 0.75 XXXVII + XVI 1 0.75 kg / ha a.S. 0.5 0.75 0.5 0.5 0.75 0.5 0.5 0.75 0.5 0.5 0.75 1 1 1 Useful plants: 0 0 0 0 0 0 0 0 0 3 0 C. 0 0 5 7th Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 10 12th Hordeum vulgar 0 0 0 0 0 0 0 0 0 0 0 5 5 0 0 0 0 0 15th 10 12th Secale cereale 0 0 10 0 15th unwanted plants: 12th 15th 0 5 10 13th 0 0 5 7th 100 100 100 100 90 90 Alopecurus myosuroides 5 7th 15th 20th 3 7th 15th 20th 3 5 7th 10 100 100 100 100 90 90 92 84 84 Poa annua 5 10 70 80 25th 46 65 75 30th 50 60 70 100 100 100 95 ! 00 100 91 100 100 Galium aparine 30 55 50 65 20th 30, 45 60 40 60 75 80 95 100 100 100 100 100 98 100 100 Lamium amplexicaule '25 30th 100 100 100

0 = without damage
100 = total damage

O.Z. 30th

cn o co

Active ingredient XXXV + XI 1 0 , 75 0 XXVII + XXII 1 0 , 75 XXVIII + XXXVI 1 0.75 XXX + XXXVII 1 0 , 75 XXIX + XXXV 1 0 , 75 XXXXIII + XXE , 5 1 0.75 XXXI + XXXVI , 5 0 1 0 9 75 Teg / ha a.S. 0.5 0.5 0 , 75 1 , 5 0.5 0 75 0.5 0.5 0.75 0.5 0.5 0 , 75 0.5 0.5 0 , 75 0 1 0.5 0.75 0 1 , 5 0 J 75 1 1 1 Useful plants: 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Triticum aestivum 0 0 0 0 0 0 0 ο 0 0 0 0 0 0 0 0 0 0 0 0 0 Hordeum vulgar 0 .0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Secale cereals 0 0 0 0 0 unwanted plants: 100 100 _ _ _ _ _ _ _ Alopecurus myosuroides 100 88 87 - 1 - _ - - - - _ - - - - - - 1 - - Poa annua 85 100 100 1 - 100 1 00 - 100 100 - 82 1 00 - 93 1 00 00 100 100 00 1 QO 1 oo G-alium aparine, 100 100 100 1 00 86 00 100 100 100 100 100 1 00 100 ! 00 1 00 1 00 100 100 1 00 00 1 00 Lamium amplexioaule 100 00 100 100 100 1 1

0 = no damage 100 = total damage

CO Cn

cn cn co

O.Z. 30 142

Active ingredient XXXIII + XXIV 1 0.75 - XVII + XXXVI 1 0 9 75 XIX + XXXVII 1 0 , 75 0 XVIII + XXII 1 0, 75 0 XVII + XXIV 0 1 0 , 75 _ XXII + XXIV 0 1 0 9 75 XIII 0.5 0.75 1 1.5 kg / ha a.S. 0.5 0.5 0.75 68 0.5 0.5 0 9 75 0.5 0.5 0 , 75 , 5 0.5 0, 75 , 5 , 5 0 , 75 - 0.5 , 5 0 f 75 1 94 1 1 1 1 90 1 Useful plants: 0 0 0 0 0 0 0 0 0 0 00 0 0 0 0 0 5 Triticum aestivum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 Hordeum vulgar 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6th Seeale cereale 0 0 0 0 0 0 unwanted plants -. mm - _ _ Alopecurus myosuroides - - - - - _- - - - 1 - - - - - _ Poa annua - 66 - 100 1 00 - 100 1 00 1 - 100 1 00 - 1 90 - 1 00 1 00 35 50 50 77 G-alium aparine 70 85 100 100 1 00 100 100 1 00 1 00 100 1 00 1 90 00 1 96 00 1 00 32 40 50 05 Lamiurn amplexicaule 100 100 100 00 00 98

0 = no damage 100 = total damage

ΙΌ CO cn

cn cn co

- 61 - O. ZOO I ¹ 12

In the G-ewach.3h.aus, different plants grew at one height from 2 to 22 cm with the following individual active ingredients and their Mixtures treated as solution-dispersion-tank mix ":

V 3,5-di,] od-4-hydroxy-benzonitrile

XXII 3,5-Dibromo-4-hydroxy-benzaldoxime-0- (2'-cyano-4 * -nitrophenyl) ether

XXI ¹ /3-Phenvl-4-hydroxy-6-chloropyridazine

XXXIV 3, 'S-dibromo - ^ - hydroxy-benzonitrile

XXXV 3,5-Diiodo-4-hydroxy-benzaldoxime-0- (2 'cyano-4 ¹ -nitrophenyl) ether

XXXVI 3,5-dibrorn-4-hydroxy-benzaldoxime-0- (2-cyano-4 ^l -nitrophenyl) -ether

XXXVII 3,5-Diiodo-4-hydroxy-benzaldoxime-0- (2'oyan-4'-nitroph-enyl ether-ilatr iunisalz

XXXVIII 3,5-dibromo-4 "hydroxy" benzonitrile lithium salt

XXXIX 3,5-dibromo-4-outanoylo.} Ty-benzonitrile

XXXX 3,5-Diiodo-4-hydroxy-benzonitrile lithium salt

with 0.25, 0.5, 0.75 and 1 kg / ha a.S.

XXXX + XXII, XXXVIII + XXXVI, XXXIX + XXXVII, XXXIV + XXXV, V + XXIV

with 0.25 + 0.75, 0.75 + 0.25, 0.5 + 0.5 kg / ha a.S.

After 10 to 1 days 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.

5098 17/1129

O.Z.JO 142

Active ingredient V 0.5 0.75 1 XXII 0.25 0.5 0.75 1 XXIV 0.25 0.5 0.75 1 XXXIV 0.25 0.5 0.75 1 0.25 XXXV 0.75 1 kg / ha a.S. 0.25 0.5 Useful plants: 0 0 10 0 0 0 0 0 0 0 0 0 5 10 15th 0 0 0 Triticum aestivum 0 0 0 10 0 0 0 0 0 0 0 0 0 0 5 10 0 0 0 0 Hordeum vulgar 0 0 0 10 0 0 0 0 0 0 0 0 0 0 5 10 0 0 0 0 Sea cereal 0 0 unwanted plants: 30th 47 60 15th 25th 70 95 5 10 15th 20th 5 20th 45 65 15th 50 63 G-alium aparine 15 30th 35 40 5 10 63 95 5 11 30th 50 10 30th 35 50 10 35 60 75 Lamium amplexicaule 20 40

= without damage
= total damage

cn cn co

O.Z.

142

CD
CD
CO

Active ingredient XXXYI 0.75 1 XXXVII 0.25 0.5 0.75 1 XXXVIII 0.25 0.5 0.75 1 XXXIX 0.25 0.5 0.75 1 XXXX 0.25 0.5 0.75 1 kg / ha a.S. 0.25 0.5 Useful plants: 0 0 0 0 0 0 0 0 0 7th 0 0 0 5 0 0 0 5 Triticum aestivum 0 0 0 0 0 0 ' 0 0 0 0 Ό 5 0 0 0 5 0 0 0 7th Hordeum vulgar 0 0 0
Ί ■ 0 0 0 0 0 0 0 0 5 0 0 0 5 0 0 0 10 Secale cereale 0 . 0 unwanted plants: 55 70 15th 25th 46 65 5 18th 35 50 5 15th 35 55 15th 28 45 60 G-alium aparine 15 30th 30th 50 10 20th 30th 45 7th 25th 30th 45 10 25th 35 47 20th 30th 35 40 Iamium amplexicaule 10 25th

= without damage
= total damage

O.Z. 30th

αϊ ο co co

Active ingredient XXXX + XXI] 0.75
0.25 0.5
0.5 XXXYIII + XXXVI 0.75
0.25 0.5
0.5 XXXIX + XXXVII 0.75
0.25 0.5
0.5 XXXIY + XXXV 0.75
0.25 0.5
0.5 V + XXIV 0.5
0.5 kg / ha as 0.25
0.75 0.25
0.75 0.25
0.75 0.25
0.75 0.25
0.75 0.75
0.25 Useful plants: 0 0 0 0 0 0 10 5 0 Triticum aestivum 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 Hordeum vulgar 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 Seoale cereale 0 0 0 0 0 0 unwanted plants: 98 95 87 88 97 78 98 94 79 Galium aparine 100 79 84 98 80 89 90 93 84 92 85 100 68 91 80
> Lamium amplexicaule 100 75 80 100 90 78

0 = no damage 100 = total damage

N> CO cn

cn cn co

Claims (5)

Claims ^rj \) A herbicide containing a mixture of in which X is chlorine, bromine, cyano, methoxy, thiomethyl, hydroxy, thioethyl, azido, R ₁ and R are the same or different and are hydrogen, a straight or branched alkyl, alkenyl or substituted by cyano, hydroxy, halogen or alkoxy Alkynyl radical with up to 7 carbon atoms, cycloalkyl, acyl, Y has the same meaning as R and R ₁ and Y also denotes alkyl, mercapto or amino and or b) a compound of the formula 0 T-R in which R is lower alkyl, R _{1 is} hydrogen and its salts c) a compound of the formula in which X is chlorine, bromine, R is acetyl, octanoyloxy, hydrogen and its salts and or - 66 5 0 9 817/1129 -.66 - CZ. 30 142 d) a compound of the formula I 000 / V-o in which X the same or different groups of chlorine, Methyl, η O to 3, R hydrogen, alkyl, m O to 2, R Denotes alkyl, hydrogen and "its salts and or e) a compound of the formula Z X in which X is lower alkyl, alkoxyalkyl, Y is hydrogen, lower alkyl, Z is hydrogen, alkyl, R is acetyl, halogen is acetyl, hydrogen and its salts and or f) a compound of the formula 0-N = CH O-R in which X is cyano, Z is hydrogen, chlorine, nitro, η O to 3, Y is halogen, R is alkyl, acetyl, haloacetyl, hydrogen and its salts and or
g) a compound of the formula 0-N = CH - 67 - 509817/1129 - 67 - OZ30 Wd. in which X is bromine, iodine, R is acetyl, haloacetyl, hydrogen and its salts " and or h) a compound of the formula OR or in which R is a lower alkyl, acetyl, halogenoetyl, an optionally substituted by nitro, trifluoromethyl sub substituted phenyl radical, -C-O-alkyl hydrogen or ti its salts "means 0 2. Herbicide according to claim 1, containing the mixtures a + b + c, a + b + e, a + b + f, a + b + g, a + b + h, a + c + d, a + c + e, a + c + f, a + c + h, a + d + e, a + d + f, a + d + h, a + e + f, a + e + h, a + f + h, a + g + h, e + f, a + f, c + h, c + f, f + h, d + f, e + h or g + h. BASF Aktiengesellschaft 5 0 9 817/1129