DE2312325A1 - HERBICIDE - Google Patents

Description

in which R is lower alkyl, cyclohexyl or a phenyl radical which is optionally substituted by halogen, and

b) a compound of the formula

in which R denotes lower alkyl up to 4 carbon atoms or their Salts, for example the alkali, alkaline earth, ammonium, hydroxyalkylammonium, alkylammonium or hydrazine salts and others, e.g. B. the salts of sodium, lithium, potassium, calcium, iron, methylamine, trimethylamine, ethylamine, Diethanolamine, kthanolamine, dimethylamine, dimethylethanolamine, Dodecylamine, decylamine, octylamine, dodecylhexamethyleneimine, Hexamethyleneimine, guanidine, hydrazine, dimethylhydrazine, phenylhydrazine, ethylhydrazine, hydroxylamine, ethylhydroxylamine,

632/72 409838/1014 / 2

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Ethylenediamine, aniline, ammonia, barium, magnesium, copper, Tin, zinc, aluminum, tripropylamine, diethylamine, butylamine, Methylallylamine, dipropylamine, diisobutylamine, amylamine, N, N-dimethyl-N- (ß-chloroethyl) hydrazine or 2-chloroethyltrimethylamine,

has a better herbicidal effect than the individual active ingredients.

The active ingredients a and b can be used in amounts of 0.1 to 5 kg / ha will.

The mixing ratio of the active ingredients a to b is 10: 1 to 1:10, preferably 3: 1 to 1: 3 parts by weight.

The mixtures are suitable for use in crops of useful plants, e.g. B. in cereal crops, such as

Avena spp. Sorghum

Triticum spp. . Zea mays

Hordeum spp. Panicum miliaceum

Seeale spp. Oryza spp.

and in cultures of dicotyledons such as Cruciferae, e.g. B.

Brassica spp. · Raphanus spp.

Sinapis spp. Lepidium spp.

Composistae, e.g. B.

Lactuca spp. Carthamus spp.

Helianthus spp. Scorzonera spp.

Malvaceae, ζ. Β.

Gossypium hirsutum Leguminosae, e.g. B.

Medicago spp. Phaseolus spp.

Trifolium spp. Araehis spp.

Pisum spp. Glycine Max

Chenopodiaceae, e.g. B.

Beta vulgar! S

Spinacia spp. Solanaceae, e.g. B.

Solanum spp. Capsicum annuum

Nicotiania spp.

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Linaceae, ζ. B.

Linum spp. Umbelliferae, e.g. B.

Petroselinum spp.

Daucus carota Rosaceae, e.g. B. Cucurbitaceae, e.g. B.

Cucumis spp. Liliaceae, e.g. B.

Allium spp. Vitaeeae, e.g. B.

Vitis vinifera Bromeliaceae e.g. B.

Pineapple sativus

unwanted plants, ζ. Β.

Agropyron repens Alopecurus myosuroides Ämaranthus spp.

Avena fatua Bracharia spp.

Artemisia vulgaris Bromus spp.

Bidens pilosa Digitaria sanguinalis Echinochloa spp.

Eleocharis palustris Eleusine indica Equisetum arvense Leptochloa spp.

Lolium spp.

Oryza oryzoides Panicum spp.

Paspalum spp.

Poa spp.

Setaria spp.

Sorghum halepense Urochloa panicoides Scirpus spp.

Apium graveolens

Pragaria

Cucurbita spp.

Abutilon theophrasti Alisma plantago Apera spied, venti Amma ^ r.ia spp. Anthemis spp. Atriplex patula Cynodon dactylon Dactylis glomerata Capsella bursa pastoris Centaurea cyanus Chenopodium album Chrysanthemum spp. Cirsium arvense Datura stramonium Euphorbia spp. Pumaria officinalis Galeopsis spp. Galinsoga parviflora Galium aparine Geranium spp. lpomoea spp. Kochia spp. Lamium spp.

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Butomus umbellatus Linaria vulgaris

Matricaria spp. Malva spp.

Mollugo verticillata Myosotis spp. ·

Nicandra physaloides. Oxalis stricta

Polygonum spp. Potulaca oleracea

Richardia scabra Papaver rhoeas

Rumex spp. - Sagittaria sagittifolia

Sesbania spp. Sida spinosa

Sinapis arvensis Sisymbrium spp.

Solanum nigrum Stellaria media

Taraxacum officinale Urtica spp "

Vicia spp. Viola tricolor arvensis

Xanthium spp.

to fight.

The mixtures can be pre-seated, pre-emerged, Post-emergence process, ULV process, granulate and scattering processes, Process during emergence, single or multiple application processes and tank mix processes (for mixtures) can be applied.

The application takes place in the form of directly sprayable solutions, Powders, suspensions or dispersions, emulsions, oil dispersions, Pastes,

Dusts, grit, granules. 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 come from medium-sized mineral oil fractions 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 methanol, ethanol, propanol, butanol, Chloroform, carbon tetrachloride, benzene, toluene, xylene, cyclohexanol, cyclohexanone, chlorobenzene, paraffin, tetrahydronaphthalene, alkylated naphthalenes, isophorone, etc., strongly polar solvents such as. B. dimethylformamide, dimethyl

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sulfoxide, etc. into consideration.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders), oil dispersions by adding water. To produce emulsions, pastes or oil dispersants, the substances as such or dissolved in an oil or solvent are homogenized in water using wetting agents, adhesives, dispersants or emulsifiers. But it can also consist of active substances, wetting, adhesive, dispersing or emulsifying agents. and possibly solvent or oil-based concentrates are prepared that are suitable for dilution with water.

The surface-active substances are alkali, alkaline earth and ammonium salts from Ligni'-ifiUlf onsSuri. N? Ph ^f : ri & - linsulphonic acids, phenolsulphonic acids, alkylarylsulphonates, alkylsulphates, alkylsulphonates, alkali and alkaline earth salts of idbutylnaphthalenesulfonic acid, lauryl ether sulfates .. fatty alcohols, fatty acid alkali and alkaline earth salts. Sri ze sulfati? Rter Hey.s.-decanols, heptadecanols, octadecanols- P-al-p of - alfa fourth fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, octylphenol ether, ethoxylated isooctylphenol, - octylphenol, - nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated ethylene oxide condensate, ethoxylated castor alcohol, ethoxylated alcohol, ethoxylated alcohol, ethoxylated alcohol, ethoxylated, ethoxylated acetyl alcohol, ethoxylated acetyl alcohol, ethoxylated acetyl alcohol, ethoxylated ethoxylacetylene, ethoxylated ethoxylacetylene, ethoxylated ethoxylated ethoxylated.

Powder and dust can be mixed or mixed Grinding the active substances with a solid excipient getting produced.

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Litter can be spread by mixing or grinding together the active substances are produced with a solid carrier.

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

Solid carriers are e.g. B. mineral earths such as Tonsil, silica gel, silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, talc, 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 cereal flours, tree bark, wood and nut shell flour, cellulose powder and other solid carriers.

Oils can be added to the herbicidal mixtures or individual products various types, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, antifoam agents (e.g. silicones), growth regulators, antidotes and others herbicidally active compounds are added and / or the same applied individually before, simultaneously and / or afterwards.

The addition of these agents to the herbicides according to the invention can be done in a ratio of 1:10 to 10: 1. The same applies to oils, fungicides, nematocides, insecticides, bactericides, Trace elements, fertilizers, anti-foaming agents and growth regulators.

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example 1

Various plants were grown in the greenhouse at a height of 3 to 15 cm with the following individual active ingredients and their Treated mixtures:

I 3-Isopropyl-2,3-benzo-thiadiazinon- (4) -2,2-dioxide 0.75, 1, 1.5, 2.25 and 3 kg / ha a. S.

II 3-Isopropyl-2,3-benzo-thiad.iazinon- (4) -2,2-dioxide-diethanolamine salt

0.5, 0.25, 0.75, 1, 1.5, 2.25 and 3 kg / ha e. S.

III 3-Isopropyl-2, l, 3-benzo-thiadiazirion- (4) -2,2-dioxide-dimethylamine salζ

0.5, 0.75, 1.5, 2.25 and 3 kg / ha a. S.

IV 3-isopropyl-2, l, 3-benzo ~ thiadiazinon- (4) - ?, 2-dioxide-. Sodium salt

0.75, 1, 1.5, 2.25 and 3 kg / ha a.S.

V 4-Amino-6-tert-butyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one

0.25, 0.75, 1, 1.5, 2.25 and; kg / na a. S.

I + V "0.75 + 0.25, 2.25 + 0.75, 0.75 + 0.7p, 0.75 + 2.25 kg / ha

a. S.

II + -V- 0.5 + 0.25, 0.25 + 0.75, 2.25 + 0.75, 0.75 - <- 0.75,

0.75 + 2.25 kg / ha a. S.

III + V 0.5 + 0.25, 2.25 + 0.75, 0.75 + 0.75, 0.75 + 2.25 kg / ha

a. S.

IV + V 0.75 + 0.25, 2.25 + 0.75, 0.75 + 0.75, 0.75 * - i, 25 kg / ha

a. S.

After 10 to 14 days it was found that the mixtures I + V, II + V, III + V and IV + V show a better herbicidal effect with the same tolerance on the crop than the individual active ingredients.

The test result can be seen from the following ΐε-belle.

409838/1014

Table 1

Active ingredient
kg / ha e. S. I.
0.75 II
0.5 III
0.5 IV
0.75 V.
0.25 I + V
0.75 + 0.25 II + V
0.5 + 0.25 III + V
0.5 + 0.25 IV + V
0.75 + 0.25 Useful plants: Solanum tuberosum
(Potatoes) 0 0 0 0 0 0 0 0 0 unwanted plants: Amaranthus retroflexus
(wire-haired amaranth) 35 30th 25th 35 30th 95 95 90 95 Chenopodiurri album
(white goose foot) 40 35 30th 35 30th 100 100 95 95 Galium aparine
(Burdock weed) 45 35 30th 40 25th 100 95 90 95 Lamiüm amplexicaule
(pigeon embracing the stem
nettle) 15th 10 10 15th 35 90 90 85 90 Matricaria chamomilla
(real chamomile) 4o 35 30th 35 30th 100 100 95 95 Xanthium pensylvanicum
(Pennsylvanian Spitz
burdock) 45 4o 35 45 20th 95 90 85 95 Alopecurus myosuroides
(Black foxtail) 10 10 10 10 40 80 80 75 80 2 Poa annua (annual
Bluegrass) 10 Ui UI 10 35 75 ' 75 70 Echinochloa crus-galli
(Chicken millet) 8th 10 10 10 40 80 80 75 ro
80 cn

-j σ \ ro

= without damage
= · Total damage

Supplement to example 1

Active ingredient 1 1.5 I. 2.25 90 3 0.25 0.75 II 1 1.5 2.25 3 0.75 1, III 3 kg / ha a. S. 100 5 2.25 Useful plants: O 0 .0 100 0 0 0 0 0 0 0 0 0 0. Solarium tuberosum 45 0 unwanted plants: 52 80 100 100 15th 40 55 8o 95 100 42 80 100 Amaranthus retroflexus 6o 90 100 100 20th 48 65 75 90 100 45 90 95 100 Chenopodium album 55 90 20th 100 15th 42 55 85 90 100 45 90 100 100 Galium aparine 20th 35 15th 6o 5 15th 20th 35 50 65 15th "^ 5 100 .65 Lamium amplexicaule 58 90 18th 100 18th 45 60 90 100 100 40 85 50 100 Matricaria chamomilla 65 95 100 20th 50 65 100 100 100 52 100 95 100 Xanthlum pensylvanicum 12th 15th 25th 5 12th 15th 15th 20th 25th 10 15th 100 20th Alopecurus myosuroides 10 15th 20th 5 12th 15th 15th 20th 25th 12th 15th 20th 25th Echinochloe crus-galli 12th 15th 20th 4th 10 15th 15 · 20th 25th 8th 15th 20th ? 3 Poa annua 20th

= without damage
= total damage

IN) CO

K) CO K)

Supplement to example 1

Active ingredient 1 1.5 IV 2.25 3 0.75 1 V 1.5 2.25 3 I + V 75 + 0.75 0.75+ kg / ha 2.25 + 0.75 0, 2.25 Useful plants: 0 0 0 0 0 15th 35 45 6o 0 Solanum tuberosum 0 35 unwanted plants: 50 75 85 100 80 95 100 100 100 100 Amaranthus retroflexus 58 90 100 100 85 100 100 100 100 100 100 ICO ο Chenopodium album 55 85 95 100 70 95 100 100 100 100 100 100 CO
00 Galium aparlne 56 95 100 100 8o 100 100 100 100 100 ' 100 100 U) Matricaria chamomilla 64 95 100 100 54 75 95 100 100 100 100 100 ' 00 Xanthium pensylvanicum 12th 15th 15th 20th 95 100 100 100 100 100 100 100 ο O Alopecurus myosuroides 10 15th 15th 20th 90 100 100 100 100 100 100 ] "00 ' Echinochloa crus-galli 12th 15th 15th 20th 95 100 100 100 100 100 100 100 Poa annua 20th 35 45 65 90 100 100 100 100 100 100 100 Lamium amplexicaule 100 100

= without damage
= total damage

K) CO K)

Supplement to example 1

O CO OD CaJ 00

Active ingredient 0.25+ II + ⁷ 7th 0.75+ 0.75+ III + V 0.75+ 0.75+ 2.25+ CV + V 0.75+ kg / ha a. S. 0.75 2.25+ 0.75 2.25 2.25+ 0.75 2.25 0.75 0.75+ 2.25 Useful plants: 0.75 0.75 0.75 Solanum tuberosum 0 0 40 0 40 0 35 unwanted plants: 0 0 0 Amaranthus retroflexus 100 100 100 100 100 100 100 Chenopodium album 100 100 100 100 100 100 100 100 100 100 Ga Hum aparine 100 100 100 100 100 100 100 100 100 100 Lamium amplexicaule 100 100 100 100 100 100 100 100 100 100 Matricaria chamomllla 100 100 100 100 100 100 100 100 100 100 Xanthium pensylvanicum 95 100 100 100 100 100 100 100 100 100 Alopecurus myosuroides 100 100 100 100 100 100 100 100 100 100 Echinochloa crus-galli 100 100 100 100 100 100 100 100 100 100 Poa annue 100 100 100 100 100 100 100 100 100 100 100 100 100

0 = s without damage 100 = total damage

PO CO

CjJ KJ

ro vo

ro

- 12 - O.Z. 29 762

Example 2

In the greenhouse, test pots were filled with loamy sandy soil and sown with various seeds. Then it became like that prepared soil treated with the following individual active ingredients and their mixtures:

I 3-Isopropyl-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide 2.5 kg / ha a. S.

II 4-amino-6-tert. -butyl-> methylthio-4,5-dihydro-1,2,4-triazin-5 * -one

0.25 kg / ha a. S. I + II 2.5 + 0.25 kg / ha a. S.

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

The test result can be seen from the following table.

Table 2

Active ingredient I - II I + II

kg / ha a. P. 2.5 0/25 2.5 + 0.25

Useful plants:

Solanum tuberosum (potatoes) 0 0 0

Zea mays (maize) 0 0 0

unwanted plants:

Gal ium aparine (Klettenlabkraut) Matricaria chamomilla (real chamomile) Sinapis arvensis (field mustard) Poa annua (annual bluegrass)

0 = no damage 100 = total damage

55 30th 95 40 40 100 40 45 100 20th 65 100

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Supplement to example 2

Active ingredient
kg / ha a. S. 0.5 1 0 2 0 2, T
5 2.75 3 4th 0 1 1.5 II
2 2.5 2.75 3 4th 0.5+
1.5 I +
3 + 1 II
1 + 3 1 + 1 Useful plants: 0 0 0 Solanum tuberοsum 0 0 0 0 15th 20th 34 4ο 47 50 SC 20th 15th 50 15th Zea mays 0 0 0 0 15th 20th 30th 40 49 54 70 20th 15th 55 15th

unwanted plants: Galium aparine Matricarla chamomilla Sinapls arvensis Poa annua

0 = no damage 100 = total damage

30 40 50 55 70 95

20 28 35 40 65 95

25 30 35 ¹ K) 65 90

5 7 10 20 20 23

95 100 100 100 100 100 100

100 100 100 100 100 100 100

100 100 100 100 100 100 100

100 100 100 100 100 100 100

100 100 100 100 I. 100 100 100 IOD 100 100 100 100 100 100 100 100 INJ
Ca)
V. O
• 12325 ΟΛ

- lh - ο.Ζ. 29 762

Example 3

In the greenhouse and in the field, various plants were grown with the following individual active ingredients at a height of 2 to 12 cm and their mixtures:

I 3-Isopropyl-2,3-benzo ~ thiadiazinon- (4) -2,2-dioxide 0.9 kg / ha a. S.

II ^ -amino-o-tert-butyl ^ -methylthio - ^ - dihydro-l ^, ^ - triazin-5-one

0.1 kg / ha a. S. I + II 0.9 + 0.1 kg / ha a. S.

After 10 to 14 days it was found that mixture I + II showed a better herbicidal effect with the same tolerance on the crop than the individual active ingredients I and II.

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

Tabel

Active ingredient I II I + II

kg / ha a. P. 0.9 0.1 0.9 + 0.1

Useful plant:

Soy hispida (soy) 0 10 10

unwanted plants:

Amaranthus retroflexus (wire-haired amaranth)

Galium aparine (burdock weed) Lamium amplexicaule (stem-encompassing Dead nettle)

Xanthium pensylvanicum (Pennsylvanian pointed burdock) Setaria viridis (green millet)

0 = no damage 100 = total damage

45 20th 95 55 15th 95 20th 30th 80 55 15th 95 10 55 90

409 83 8/1014 Λ5

1 15 - 2 0 0.2 II o.z. 2 29 762 1 23 12325 Active ingredient O· I. 100 15th 100 I + II kg / ha a. S. 1.8 95 75 1.8 + 0.2 Useful plants: 50 55 35 100 SoYes hispida 55 0 100 25th 95 100 15th unwanted plants: 20th 15th 60 95 100 Amaranthus retroflexus 10 90 25th 100 100 100 Galiura aparine 65 90 40 100 100 100 Lamium amplexieaule 50 75 100 Setaria viridis 15th 100 Xanthium pensylvanicum 95 100

0 = no damage 100 = total damage

Example 4

In the greenhouse, test pots were filled with loamy sand soil and sown with various seeds. Then the soil prepared in this way was treated with the following individual active ingredients and their Treated mixtures:

1 3-isopropyl-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide, 2.5 kg / ha a. S.

II 4-Amino-6-1 tert-butyl-> methyl thio-4,5-dihydro-1,2,4-triazin-5-one

0.25 kg / ha a. S. I + II 2.5 + 0.25 kg / ha a. S.

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

The test result can be seen from the following table.

40 98 38/101 L / 16

- 10 - 20th II
0.25 O.Z. 29 762 2312325 Table 4 0 Active ingredient
kg / ha a. S. I.
2.5 I + II
2.5 + 0.25 Useful plant: 30th Soy hispida (soy) 0 40 0 unwanted plants: 45 Galium aparlne
(Burdock weed) 55 65 95 Matricaria chamomilla
(real chamomile) 40 100 Sinapis arvensls (field mustard) 40 100 ' Poa annua (annual
Bluegrass) 100

0 = no damage 100 = total damage

40 9 8 38/1014

Claims (2)

- 17 - O. Z. 29 762 Claims Q). A herbicide containing a mixture of a) a compound of the formula SCH, ' in which R is lower alkyl, cyclohexyl or optionally one is a halogen-substituted phenyl radical and b) a compound of the formula in which R is lower alkyl up to 4 carbon atoms or their Salts. 2. Herbicide according to claim 1, containing a mixture of 3-isopropyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide and triazin-5-one. Badische Anilin- & Soda-Fabrik AG 409838 / TO 14