DE2351607A1 - Weed control with polychloroallyl N,N-diisopropyl-thiocarbamate - in conjunction with 4-amino-5-chloro-6-pyridazone - Google Patents

Abstract

Weed control amongst crop plants is effected by (a) treating the soil with a cpd. of formula (I): (i-Pr)2N-CO-S-CH2-CCl=C(R)Cl (where R is H or Cl) and/or with 1-phenyl-4-amino-5-chloro-6-pyridazone (II) before or directly after sowing the crop, and (b) treating with (II) after the emergence of the weeds. The process can be used for the selective control of a wide range of mono- and dicotyledonous weeds, e.g. of Avena fatua, Alopecurus myosuroides and Matricaria chamomilla in beet crops.

Description

Our reference: QZ 30 144 Sws / UB 6700 Ludwigshafen, October 9, 1973

It is known that pyridazones and thiol carbamates have a herbicidal effect. However, their herbicidal effects are not always sufficient.

A method for controlling unwanted plants has been found in which one takes place before or immediately after sowing the crop plants the soil in which the growth of the unwanted plants is to be prevented

a) a compound of the formula

0H ~ - ^. p ". R.

HGS-GH ₀ -OGl = O-Gl ^ 0

in which R is hydrogen or chlorine and / or

b) the connection

1-phenyl-4-amino-5-chloro-pyridazon- (6)

and after the appearance of the unwanted plants the soil with it

c) the connection

1-phenyl-4-amino-5-chloro-pyridazon- (6)

treated, whereby the unwanted plants are destroyed while the useful plants grow without damage.

The amount of active ingredients used can vary. The amount used depends mainly on the type of effect desired. The application rate is generally between 0.1 and 30 or more, preferably 0.2 to 6 kg of active ingredient per hectare.

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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 watering. The application forms depend entirely on the intended use, they should in any case be as finely distributed as possible ensure 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, tetrahydronaphthaline, 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-methylpyrilidone, water etc. in 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 will. But it can also consist of active substances, wetting agents, adhesives, dispersants or emulsifiers and possibly Solvent or oil-based concentrates can be prepared, which 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 Dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol

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sulfates, fatty acid alkali and alkaline earth salts, sulfated salts Hexadecanols, heptadecanols, octadecanols, salts of sulfated em 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, polyoxyethylene-oetylphenolether, ethoxylated isookty! phenol, - Ocjbylphenol-, 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 methvlcellulose.

Powder, litter and dust can be produced by mixing or grinding together the active substances with a solid Carrier are produced.

Granules, e.g. TJmhüllung3-, impregnation and homogeneous granules, can be produced by binding the active ingredients to solid carriers. Solid carriers are e.g. mineral earth such as 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 cereal flours, tree bark, wood and nutshell 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.

In addition to the mixtures or individual active ingredients, oils can be different Type, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, antifoam agents (e.g. silicones), Growth regulators, antidotes, or other herbicidal

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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 benzthiadiazinone dioxides substituted benzoxazines substituted benzoxazinones substituted benzthiadiazoles 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

substituted Oycloalkylcarbonamido-thiazoles substituted dicarboxylic acids and salts, esters and amides substituted dihydrobenzofuranylsulfonate substituted disulfides
substituted dipyridylium salts
substituted dithiocarbamates

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

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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 phosphonaltcylglyzines substituted phosphites

substituted phosphoric acids and their salts, esters and amides

substituted piperidines substituted pyrazoles

substituted pyrazole alkyl carboxylic acids and their salts, esters and amides

substituted pyrazolium salts substituted pyrazolium alkyl sulfates substituted pyridazines substituted pyridazones

substituted pyridinoarboxylic acids and their salts, esters and amides

substituted pyridines substituted pyridine carboxylates substituted pyridinones substituted pyrimidines substituted pyrimidones

substituted pyrrolidinecarboxylic acid and its salts, esters and amides

substituted pyrrolidines substituted pyrrolidones

substituted arylsulfonic acids and their salts, esters and amides

substituted styrenes' substituted tetrahydro-oxadiazinediones

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substituted tetrahydro-oxadiazole dione substituted tetrahydromethanoindenes substituted tetrahydro-diazol-thiones substituted tetrahydro-thiadiazine-thiones substituted tetrahydro-thiadiazole dione substituted aromatic thiocarboxamides

substituted thiocarboxylic acids and their salts, esters and amides

substituted thiocarbamates substituted thioureas

substituted thiophosphoric acids and their salts, esters and amides

substituted triazines substituted triazoles substituted uracils ■ substituted uretidinediones

possibly also immediately before use (Tanlcmix) can be added. The herbicidal compounds mentioned last can also be used before or after the individual active ingredients according to the invention or mixtures can be used.

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

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

Weeds or unwanted vegetation are to be understood as meaning all monocotyledonous and dicotyledonous plants that are in places grow up where they are not wanted.

For example, with the agents according to the invention

509816/1157 ~ ⁷ ~

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Gramineae, how

Cynodon spp. Digitaria spp. Echinoohloa spp. Setaria spp. · Panicum spp. Alopecurus spp. Lolium spp, Sorghum spp. Agropyron spp. Phalaris spp. Apera spp.

Cyperaceae, like

• Carex spp. Gyperus spp. Seirpus spp.

dicot weeds, like

Malvaceae, e.g.

Abutilon theoprasti Sida spp. Malva spp.

Compostiae, like

Ambrosia spp '. Lactuca spp. Senecio spp. Sonchus spp. Xanthium spp. Iva spp. G-alinsoga spp. Taraxacum spp. Chrysanthemum spp. Bidens spp. Cirsium spp.

+) Phragmites communis Dactylis spp. Avena spp. Bromus spp. üniola spp. Poa spp.
Leptoenloa spp. Brach-iaria spp. Eleusine spp. Ceηehrus spp. Eragrostis spp, and others

Eleoeharis spp, and others

Hibisous spp. and other

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

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Convolvulaceae, like

Convolvulus spp. Ipomoea spp. Jaquemontia tamnifolia

Cruciferae, like

Barbarea vulgaris Brassica spp. Capsella spp. Siaymbrium spp. ThIaspi spp. Sinapis arvensis Raphanus spp.

G-eraniaceae, like

Erodium spp. Geranium spp.

Portulacaoeae such as Portulaca spp.

Primulaceae, like

Anagallis arvensis Lysimachia spp.

Rubiaceae, like

Richardia spp. Galium spp.

Scrophulariaceae, such as

Linaria spp. Veronica spp.

Sdlanaceae, like

Physalis spp. Solanum spp. Datura spp. Cuscuta spp. and other

Arabidopsis thaliana Descurainia spp. Draba spp. Coronopus didymus ■ Lepidium spp. and other

and other

and other

and other

Diodia spp. and other

Digitalis spp, and others

Nicandra spp. and other

509816/1

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Urticaoeae such as Urtica spp.

Violaceae such as Viola spp.

Zygophyllaceae such as Tribulus terrestis

EuphorMaoeae, such as Mercurialis annua

Umbelliferae, like

Daucus carota Aethusa cynapium

Commelinaeae Commelina 3pp.

LaMatae, like

Lamiuin spp. Galeopsis spp.

Leguminosae, like

Medicago spp. Trifolium spp. Ticia spp. Lathyrus spp.

Plantaginaceae such as Plantago spp.

Polygonaceae, like

Polygonum spp. Rumex spp.

Aizoaceae, like and others and other Euphorbia spp,

Ammi majus and others

and others and others

Sesbania exaltata Gassia spp. and other

and other

Pagopyrum spp, and others

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Mollugo verticillata

Amaranthaceae such as Amaranthus spp.

Boraginaceae, like

Amsinckia spp. Myostis spp. Lithospermum spp.

Garyophyllaceae, such as

Stellaria app. Spergula app. Saponaria spp. Scleranthus annuus

Ghenopodiaceae, such as

Ghenopodium spp. Kochia app. Salsola Kali

Lythraceae, like Cuphea app.

Oxalidaceae such as Oxalis spp.

Ranunoulaoeae, like

Ranunculus spp. Delphinium spp.

Papaveraceae, like

Papaver spp. Fumaria officinalis

Onagraceae such as Jussiaea spp. and other

and other

Anchusa spp. and other

Silene spp. Gerastium spp. Agrostemma pallida and other

Atriplex spp. Monolepsis nuttalliana and others

and other

Adonis app. And others

and other

and other

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Rosaceae, like

Alchemillia spp. Potentilla spp.

Potamogetonaceae such as Potamogeton spp.

Najadaeeae such as Najas spp.

Marsileaceae, such as Marsilea quadrifolia

Polypodiaceae, 'such as Pteridium aguilinum

Alismataceae such as Alisma spp.

Sagittaria sagittifolia

Equisetaceae such as Equisetaceae 3pp.

be fought.

and other

example 1

and others and others and others

and others and others

In the greenhouse, loamy sandy soil was poured into Yersuchs pots and sown with various seeds. Treatment with the active ingredients

I N, N-Diisopropyl-thiplcarbamic acid-2,3-dichloroallyl ester

II NjN-Diisopropyl-thiolcarbamic acid-i, 3,3-trichloroallyl ether

III 1-phenyl - ^ - amino-S-chloropyridazon- (6)

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

was done as follows:

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A treatment with active ingredient I and II incorporated as an emulsion before sowing;

B treatment with active ingredient III as a dispersion after Sowing the crop;

C Treatment with active ingredients I or II incorporated before sowing as well as additional treatment with active ingredient III after sowing the crop and in comparison with treatment A with active ingredient IV,
B with the active ingredient III,

C with the active ingredient I? as treatment A + active ingredient III as treatment B.

The table below shows that the treatment method C of I or II with III compared to IV and III a better tolerance on the crop plants with the same herbicidal Shows effect.

The test result can be seen from the following table.

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Treatment method 1.5 1.6 I. 2.4 3 A. 4th 1 1.5 1.6 II 2.4 3 4th IV B. 1 1.5 1.6 2 2.4 3 4th 5S ₁ 75 Active ingredient 2 2 1.6 III 50 kg / ha a.S. 1 0 0 13th 15th 20th 0 0 0 8th 10 15th 0 0 0 0 0 0 10 100 Useful plants: 10 7th 75 Beta vulgaris 0 83 86 98 100 100 67 90 91 99 100 100 12th 15th 17th 20th 30th 40 unwanted plants: 87 90 95 96 100 100 60 90 95 98 100 100 100 85 15th 19th 19th 23 26th 30th Avena fatua 60 13th 15th 94 25th 30th 40 12th 15th 17th 100 27 32 45 75 50 60 65 85 95 100 Alopecurus myosuroidea 58 19th 21 100 Matricario chamomilla 10

0 = no damage 100 = total damage

O.Z. 30th

αϊ ο co οο

Treatment method I + III 1 + 2 2 + 1 1.5 + 1.5 1.6 + 2.4 C. II + III 1 + 2 2 + 1 1.5 + 1.5 1.6 + 2.4 ■ IV + III Active ingredient 1.6 + 2.4 kg / ha a.S. O 10 0 0 0 7th 0 0 Useful plants: 75 Beta vulgaris 100 100 100 100 100 100 100 100 unwanted plants: 100 100 100 .100 100 100 100 100 100 Avena fatua 100 95 98 100 100 98 100 100 100 Alopecurua myosuroides 100 Matricaria chamomilla

0 = no damage 100 = total damage

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example 2

In the greenhouse, loamy sandy soil was poured into experimental pots and sown with various seeds. Treatment with the active ingredients

I N.N-Diisopropyl-thiolcarbamic acid - ^, 3-dichloroallyl ester

II N.N-Diisopropyl-thiolcarbamic acid ^^^ - trichloroallyl ester

III 1-phenyl-4-amino-5-chloro-pyridazon- (6)

was done as follows:

A treatment with active ingredient I and II incorporated before sowing;

B treatment with active ingredient III after sowing the crop plants;

C Treatment with active ingredients I or II incorporated before sowing and additional treatment with active ingredient III after sowing the crop.

The table below shows that the treatment method G compared to treatment methods A and B a better herbicidal effect with the same tolerance to the Crops showed.

The test result can be seen from the following table.

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Treatment method 1 I. 2 A. II 0.5 1 1.5 2 B. 0.5 1 [II 2 C. I + III 1.5 + 0.5 1 + 1 II + III 1.5 + 0.5 1 + 1 Active ingredient 1.5 1.5 0.5 + 1.5 0.5 + 1.5 kg / ha a.S. 0.5 0 10 0 0 0 7th 0 0 0 0 0 0 0 Useful plants:
cn ^r 0 0 0 0 O
cd Beta vulgaris 0
OO σ> 60 95 25th 67 90 98 2 12th 20th 100 100 100 98 ~ * unwanted plants: 58 83 94 30th 60 90 100 2 15th 15th 23 65 100 100 73 100 100 * fl Avena fatua 20 10 87 19th 9 12th 15th 21 25th 50 I9 85 74 68 93 80 73 93 Alopecurus myosuroides 26 13th 60 95 98 Matricaria chamomilla 5

= without damage
= total damage

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Example 3

In the greenhouse, loamy sandy soil was poured into experimental pots and sown with various seeds. Treatment with the active ingredients

I N, N-Diisopropyl-thiolcarbamic acid 2,3-dichloroallyl ester

II N, F-Diisopropyl-thiolcarbamic acid-2,3,3-trichloroallyl ether

III 1-phenyl-4-amino-5-chloropyridazon- (6)

was done as follows:

A treatment with active ingredient I and II incorporated before sowing;

B treatment - with the active ingredient III after the emergence of the weeds;

C Treatment with active ingredients I or II incorporated before sowing 3 as well as additional 'treatment with active ingredient III after the weeds emerge.

The table below shows that the treatment method C has a better herbicidal effect compared to treatment methods A and B with the same tolerance to the Crops showed.

The results of the search can be seen from the following table.

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Treatment method

Active ingredient

II

III

Γ + III

II + III

kg / ha a.S.

cn crops;
O

-η Beta vulgaria

0.5

unwanted plants:

Avena fatua

20th

Alopecurus myoauroides 26 Matricaria chamomilla 5

60 58 10

1.5

83 87 13

0.5

10

95 94 19

25 30

67 60 12

1.5

90 90

15th

0.5

98

ti

21

11
5

35

12 35

45

1.5

0.5 + 1.5

65
95
80

1.5 + 0.5

100

100

83

1 + 1

0.5 + 1.5

98

hoo

88

73
97
90

1.5 + 0.5

100

100

84

0 = no damage 100 = total damage

- 19 - OZ 3C l44

Example 4

In the greenhouse, loamy sandy soil was poured into Versuohs pots and sown with various seeds. Treatment with the active ingredients

I NjN-Misopropyl-thiolcarbamic acid Z ^ -dichloroallyl ester

II N _f N-Diisopropyl-thiolcarbamic acid 2,3,3-trichloroallyl ester

III i-phenyl-4-amino-5-chloro-pyridazon- (6)

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

was done as follows:

A treatment with active ingredient I and II incorporated before sowing;

B treatment with active ingredient III after the weeds emerge;

C Treatment with active ingredients I or II before sowing incorporated as well as additional treatment with the active ingredient III after weeds emerge;

and compared with

Treatment A with the active ingredient IV ff B "" "III

"C" "" IV as treatment A + active ingredient

III as treatment B.

The table below shows that the treatment method G from I or II with III compared to IV + III a better tolerance on the crop plants with the same herbicidal Shows effect.

The test result can be seen from the following table.

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Treatment method 1.5 1.6 I. 2 2.4 3 A. 1 1.5 1.6 ΙΊ 2 2.4 3 4th IV B. III 1 1.5 1.6 2 2.4 3 4th Active ingredient 1.6 \ rg / ha a.S. 1 0 0 10 13th 15th 4th 0 0 0 7th 5 10 15th 0 0 0 0 0 0 10 Useful plants:
απ "■" ■ ' * 75 O
^ O Beta vulgaris 0 20th OO cn 83 86 95 98 100 67 90 91 98 100 100 100 12th 15th 17th 22nd 30th (40) 65 _ * unwanted plants: 87 90 94 96 100 60 90 95 100 100 100 100 85 35 38 38 40 57 80 95 ⁱⁿ Avena Fatua 60 13th 15th 19th 25th 30th 100 12th 15th 17th 21 27 32 45 75 45 50 53 60 70 90 100 Alopecurus myosuroides 58 100 100 Matricaria chamomilla 10 40

= without damage
= total damage

-) * CD O

O.Z. 30 144

Treatment method I + III 1.6 + 2.4 G 1 + 2 II + III 1.6 + 2.4 IV + III Active ingredient. 2 + 1 1.5 + 1.5 0 0 2 + 1, 1.5 + 1.5 0 1.6 + 2.4 \ cg / ha a.S. 1 + 2 10 0. 7th 0 75 Useful plants:
cn
® Beta vulgaris. 0
co 100
. 100
100 100
100
100 100
100
100 - * unwanted plants: VD O O
O O O VD O O
O O O 100
100
95 100
100
95 100
100
100 in
* j Avena fatqa. 95
Alopecurus myosuroides 100
Matricaria chamomilla 100

0 = without damage
100 = total damage

Claims (1)

- 22 - O.Z. 3C 144 Claim A method of combating undesirable plants, characterized in that, before or directly after sowing the crop plants, the soil in which the growth of the undesired plants is to be prevented is added a) a compound of the formula ^ NCS-CH ₀ -CCl = C-Cl rar ^ - "κ έ- - ^Gil O in which R is hydrogen or chlorine and / or b) the connection 1-phenyl-4-amino-5-chloropyridazon- (6) and after the appearance of undesirable plants with c) the connection 1-phenyl-4-amino-5-chloro-pyridazon- (6) treated. BASF Aktiengesellschaft, 509816/1157