DE2165555A1 - METHOD OF CONTROLLING UNWANTED PLANT GROWTH - Google Patents

Description

Badische Anilin- & Soda-Fabrik AG

Our reference : 0.Z.2J 891 Sws / Wil 6700 Ludwigshafen, December 27th, 1971

Method of combating unwanted vegetation

The present invention relates to a method for controlling undesired vegetation using benzothiadiazinone dioxide derivatives.

It is known that 5-isopropyl-2, l,; 5-benzo-thiadiazinon- (4) -2,2-dioxide to use as a herbicide. The active ingredient is injected onto the leaves of green plants.

It has been found that unwanted vegetation is combated, when you put the seeds of unwanted plants in the soil with a benzo-thiadiazinone dioxide derivative of the formula

where R is a lower alkyl radical with up to 4 carbon atoms or the cyclohexyl radical, or treats the salts of this compound, when the majority of the seeds are in the dormancy, germination or emergence stage.

By lower alkyl radicals with up to 4 carbon atoms we mean the methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl radical. Unwanted plants are all plants whose growth is to be prevented on a certain area of the soil. The majority are 50 % or more. Dormancy is the normal condition of the seeds when they are kept dry. The seeds can be kept in this state for a long time, for example over several vegetation periods, without germination occurring. The germination stage is understood to mean both the beginning of germination, i.e. absorption of moisture by the seed, swelling of the seed,

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Beginning of the development of the germ, breaking through of the germ the seed coat until germination is complete, d. H. until the plants are nourished by the roots and no longer by the Nutrient supply of the seed takes place. Emergence is the breaking through of the seedling through the surface of the earth.

The active ingredient can be used in a variety of ways. For example you can introduce the active ingredient into the soil before sowing and then the seeds into the soil sow. The active ingredient can also be introduced immediately after the seed or later in the soil. The latest time is reached when the majority of the seeds are no longer in the state of germination, i.e. H. germination has finished.

The method is suitable for controlling the following undesirable plants:

Alisma plantago-aquatica Ammannia coccinea Amaranthus spp. Anthemis spp. Butomus umbellatus Centaurea cyanus Chenopodium album Chenopodium spp. Chrysanthemum spp. Cyperus spp. Galeopsis spp. Galinsoga parviflora Galium aparine Geranium spp. Matricaria spp. Papaver rhoeas Polygonum spp. Portulaca oleracea Raphanus raphanistrum Sagittaria sagittlfolia Sida spinosa Sinapis arvensis

Water frog spoon We have grown amaranth species Dog chamomile species swan flower cornflower white goosefoot goosefoot species wildflower species Sedge grass species hollow tooth species small-flowered French herb sticky herb Cranesbill species Camomile species Corn poppy Knotweed species Cabbage purslane Hederich Arrow herb thorny velvet poplar Mustard

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Stellaria media Xanthium spp.

Scirpus spp.

Lapsana communis Sesbania exaltata being the crops; Gossypium hirsutum Phaseolus vulgaris Pisum sativum Arachis hypogaea Cucumis sativus Solanum tuberosum Trifolium Linum usitatissimum Medicago sativa Zea mays

Daucus carota Oryza sativa Soy (Glycine) hispida Sorghum bicolor Allium cepa

not be harmed.

Chickweed Pointed burdock species Rush species Rain cabbage Legume species,

Cotton beans, peas, peanuts, cucumbers, potatoes, clover, flax, alfalfa Corn Carrots Rice Soy Sorghum Onions Grain

The active ingredients can be present in known "distribution forms, for example as an aqueous solution, dispersion or emulsion made from water and active ingredient with the aid of conventional dispersants or as a solution in organic liquids or as a dispersion in an "organic liquid, for example in paraffin oil, or as dust or as granules. Wetting agents or other oils can also be added will.

By salts we mean, for example, the alkali, alkaline earth, Ammonium, hydroxyalkylammonium, alkylammonium, fatty amine or hydrazine salts, e.g. B. salts of ammonia, barium, magnesium, Copper, tin, zinc, aluminum, sodium, lithium, potassium, calcium, iron, methylamine, trimethylamine, ethylamine, diethanolamine, Ethanolamine, dimethylamine, dimethylethanolamine, dodecylamine,

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Decylamine, octylamine, dodecy! Hexamethyleneimine, hexamethyleneimine, Guanidine, hydrazine, dimethylhydrazine, phenylhydrazine, ethylhydrazine, Hydroxylamine, ethy! Hydroxylamine, ethylenediamine, aniline, Tripropylamine, diethylamine, butylamine, methylallylamine, dipropylamine, Diisobutylamine, amylamine, N, N-dimethyl-N- (ß-chloroethyl) hydrazine or 2-chloroethyl trimethylamine.

To improve the effect it is possible after some time treatment of the seeds to treat the green leaves of the plants that have developed in the meantime with the active ingredient. on in this way, a further enhancement of the herbicidal action against undesired plants is achieved.

In addition, the active ingredient can improve the herbicidal effectiveness with other herbicidal active ingredients, e.g. B. substituted thiol carbamates, substituted carbamates, substituted azepine carbothioates, substituted nitroanilines, substituted phenyl ethers, chlorinated fatty acids and their esters, substituted Benzoic acids and substituted haloacetylanilides can be mixed.

The following examples explain the process according to the invention.

example 1

In the greenhouse, experimental pots were filled with loamy sandy soil and the seeds of Zea mays, Soja hispida, Gossypium hirsutum, Stellaria media, Matricaria chamomilla, Chenopodium album and Amaranthus retroflexus were sown. Then the floor was each with 2; 3; 4; 6 kg / ha of the active ingredient 3-isopropyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide (I) compared to 6 kg / ha of the active ingredient N-isopropyl-of-chloroacetanilide (II) as Granules treated.

After 4 to 5 weeks, those listed in the table below became Results found:

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kg / ha active ingredient 2 40 I.
3 4th 6th II
6th Zea mays (corn) 0 20th 0 0 0 10 Soy hispida (soy) 0 0 0 0 20th Gossypium hirsutum (cotton) 0 0 0 5 20th Stellaria media (chickweed) 60 70 80 90 70-80 Matricaria chamomilla (eohte
Chamomile) 65 75 8o 90 80 Chenopodium album (white goosefoot) 70 75 8o 90 8O-9O Amaranthus retroflexus
(wire-haired amaranth) 50 6o 80 7O-8O Sinapis arvensis (field mustard) 35 6o 90 60

0 = without damage
100 = total damage

Example 2

In the field 3 days after the sowing of Hordeum vulgar, Triticum aestivum, Sinapis ar.vensis, Matricaria chamomilla and Stellaria media the soil with the active ingredients

1; 5-isopropyl-2,3-benzo-thiadiazinon- (4) -2,2-dioxide

II 3-Isopropyl-2, l, j5-benzo-thiadiazinon- (4) -2,2-dioxide sodium salt

III 3-Isopropy1-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide dimethylamine salt

compared to

IV N-N-Diisopropyl-thiolcarbamic acid-2, j5,; 5-trichloroallyl ester dissolved or emulsified in an amount of 6 kg / ha of active ingredient treated in 500 liters v / ater per hectare. It was observed that individual weeds germinated and then died. After 3 weeks the plants in the treated plots were counted and compared with an untreated plot.

The result is shown in the table below.

Active ingredient

I II III IV acts pc. Pc. Pc. Pc.

Hordeum vulgar (barley) 46 44 4 ^ 25 45 Triticum aestivum (wheat) 42 40 44 22 42 Sinapis arvensis (field mustard) 4 6 3 30 29

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Active ingredient

I II III IV acts pc. Pc. Pc. Pc.

Matricaria chamomilla (real chamomile)

Stellaria media (chickweed)

3 2 3 1 14th 17th ere) 4th 7th 3 32 37 example

In the greenhouse, 20 × 20 × 15 cm large test vessels were used clay soil and the seeds of Oryza sativa (rice), Alisma plantago (water frog spoon), Polygonum persicaria (Flea knotweed), Amaranthus retroflexus (wire-haired amaranth) sown and the soil surface with 6 kg / ha active ingredient 3-isopropyl-2,3-benzo-thiadiazinon- (4) -2,2-dioxide dispersed in 500 liters of water per hectare treated. The surface was then flooded with water to a height of 10 cm. After 3 to 4 weeks it was found that Oryza sativa showed normal growth, while Amaranthus retroflexus, Polygonum persicaria and Alisma plantago aquatica were almost dead.

Example 4

In the open ground, a 2 m large plot was planted with the seeds of Zea mays (maize), Triticum aestivum (wheat) and Matricaria chamomilla (real chamomile), Stellaria media (chickweed) and Sinapis arvensis (mustard).

After the majority of the seeds of the unwanted plants in the Soil was in the state of germination and Zea mays and Triticum aestivum had just emerged, the soil surface became with 4 kg / ha active ingredient 3-isopropyl-2,3-benzo-thiadiazinon- (4) -2,2-dioxide (i) dispersed in 500 liters of water per hectare treated.

The test result can be found in the following table '(average of three tests)

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Number of plants

on the day of
treatment 21
7 days after
the treatment
lung 65555
24 days
after
treatment 15th 15th 18th 38 39 43 12th 4th 2 9 4th 3 17th 4th 1

Zea mays (Mals)

Triticum aestivum (wheat)

Matricaria chamomllla (real chamomile)

Stellaria media ("chickweed") Sinapis arvensis (field mustard)

Number of plants

untreated on the day of the 7 days after 24 days Treatment of the hand after the

lung treatment

Zea mays (corn)

Triticum aestivum (wheat)

Matricaria chamomilla (real chamomile)

Stellaria media (chickweed) Sinapis arvensis (field mustard)

15th 16 17th en) 38 39 42 12th 17th 26th lere) 8 13th 21 ■ mustard) 16 25th 36 Example 5

In the Preiland the seeds of Oryza sativa (rice), soy hispida (soy), Solanum tuberosum (potatoes), Chenopodium album (white goosefoot), Sida spinosa (thorny pollen), Amaranthus retroflexus (wire-haired amaranth) , Portulaca oleracea (cabbage purslane), Galium aparine (sticky herb), Sinapis arvensis (field mustard) and Cyperus esculentus (tiger nut) and then sown the soil surface with 3 kg / ha of active ingredient 3-isopropyl-2, l, 3-benzo-thiadiazinone - (4) -2,2-dioxide treated as granules. After 3 weeks it was found that Oryza sativa, Soja hispida, Solanum tuberosum continued to grow without damagej showed slight damage up to 30 % Cyperus esculentus, Portulaca oleracea, Galium aparine. Amaranthus retroflexus and Chenopodium album were damaged in 50 to 70 % , while Sida spinosa and Sinapis arvensis were damaged in 80%.

At this point in time, the leaves of the plants were treated with 1.5 kg / ha of active ingredient 3-isopropyl-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide treated as a dispersion in 500 liters of water per hectare.

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After another 14 days it was found that Oryza sativa, Soja hispida, Solanum tuberosum continued to grow without damage, while the weeds Chenopodium album, Slda spinosa, Amaranthus retroflexus, Portulaca oleracea, Galium aparine, Slnapis arvensls and Cyperus esculentus were completely dead.

Example 6

In the Preiland a plot of 2 m with 6 kg / ha of active ingredient was created 3> -Isopropyl-2,3-benzo-thiadiazinon- (4) -2,2-dioxide, dispersed in 500 liters of water. After 15 days the seeds became from Zea mays (maize), Oryza sativa (rice), Hordeum vulgare (barley), Triticum aestivum (wheat), soy hispida (soy), Matricaria chamomiila (real chamomile), Sinapis arvensis (field mustard) and Stellaria media (chickweed) sown. During the test period of 24 days it was irrigated daily with ^ mm of water.

After 24 days the weeds Matricaria chamomiila, Sinapis arvensis and Stellaria media were almost completely dead, while Zea mays, Oryza sativa, Hordeum vulgare, Triticum aestivum and soy hispida continued to grow with practically no damage.

Example 7

Solanum tuberosum were found on a trial area in the field (Potatoes). Unwanted plants such as Raphanus raphanistrum (Hederich), Sinapis arvensis (field mustard) and Stellaria media (chickweed), which emerged before the potatoes, were treated with jü kg / ha active ingredient of the compound 3-isopropyl-2, l, 3-benzo-thiadiazinon- (4) -2,2-dioxide, dispersed in 500 liters of water per hectare, treated. A few days after the treatment, the unwanted plants began to die. 2 to J5 weeks later the unwanted plants had completely died; meanwhile the potatoes could do without any harm germinate and grow.

Example 8

In the greenhouse, loamy sandy soil was placed in test pots.

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fills and with the seeds of Oryza sativa (rice) and the tubers of Cyperus escuientus (earth almond) and Cyperus rotundus (round Cypergrass) sown. Thereafter, the treatment with the active ingredient 3-isopropyl-2,3-benzo-thiadiazinon-(4) -2,2-dioxide was carried out as follows performed;

A 3 kg / ha active ingredient after sowing

B 3 kg / ha active substance after sowing + 1 kg / ha active substance 3 weeks after the first treatment

C 3 kg ha active substance after sowing + 1 kg / ha active substance 3 weeks after the first treatment + 1 kg / ha active ingredient 8 days after the 2nd treatment,

each dispersed in 500 liters of water per hectare.

The test result can be seen from the following table.

Treatment type A BC

kg / ha active ingredient 3 3 + 1 3 + 1 + 1

Oryza sativa (rice) 0 OQ

Cyperus escuientus (Tigernuts) 20 - 30 80 100 Cyperus rotundus (round cypergrass) 10 50-60 90

0 = without damage
IQO = total damage

In Examples 1 to 8, the following compounds are biologically active as I;

3-isopropyl-2,1,3-benzo-thladlazinon- (4) -2 _J, 2-dioxide-2-chloräthyltrimethy! Ammonium salts

3-isapropyl-2,1 _J , 3-benzo-thiadiazinon- (4) -2,2-dioxide-N, N-dimethyl-N-i3 -chloroethylhydra zoniunsalz ,

3-isopropyl-2,1 _J 3-t ^> enzo-thiadiazinon- (4) -2 ₁ 2-dioxide-trimethylethanolamine salt,

3-isopropyl-2, l, 3-benzo-thiadiazinon- (4) -2 _i 2 ~ dioxide-ammonium salt, 3-isoprop; yl-2, l, 3-benzO-thiadiazinon- (4) -2,2- dioxide-ethanalamin-

3-methyl-2,1,3-benzo-thiadiazinon- (4) _-2,2: ethanolamine dioxide _{J (3-ttthyl-2, J} l, 3-benzo-thia <iiazinQn-i4J _s 2. _J1 2-dioxide,

3 0 9 8 2 9/1 υ 9 4

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3-Kthyl-2,1,3-benzo-thiadiazinon- (4) -2, 2-dioxide sodium salt, 5-ethyl-2, l, 3-benzo-th.iadiazinon- (4) -2 _J 2- dioxide-2-chloroethyltrimethylammonium salt,

3-propyl-2 _J 1,3-benzo-thiadiazinon- (4) ~ 2,2-dioxide _J 3-propyl-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide sodium salt, 3-propyl-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide-triethylamine-

3-isobutyl-2,1,3-benzo-thiadiazinon- (4) -2,2-dioxide, 3-isobutyl-2, l _i 3-benzo-thiadiazinon- (4) -2,2-dioxide sodium salt, 3-sec-butyl-2,1, J-benzo-thiadiazinon- (4) -2,2-dioxide.

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Claims (1)

Claims 1. A method for controlling unwanted vegetation using benzothiadiazinone dioxide derivatives of Pprmel JC. where R is a lower alkyl radical with up to 4 carbon atoms or denotes the cyclohexyl radical, or their alkali, alkaline earth, Ammonium, hydroxyalkylammanium, alkylammonium, fatty amine or hydrazine salts by treating the seeds of undesired plants in the soil when the majority of the seeds are in the Stage of dormancy, germination or emergence. 2. The method according to claim 1, characterized in that the seeds in the soil according to claim 1 and later the leaves of the green plants are treated with the active ingredients mentioned in claim 1 first. 5. The method according to claim 1, characterized in that 5-isopropyl-2, l, 3-benzothiadiazinon- ( ² r) -2,2-dioxide is used as the active ingredient. 2-way φ _t - ■ 309829/1094