DE2164460A1 - USE OF A UREA DERIVATIVE AS A HERBICIDE - Google Patents

Description

Badische Anilin- & Soda-Fabrik AG 2164460

Our reference: O.Z. 27 88I Sws / Wil 67OO Ludwigshafen, December 22nd, 1971

Use of a urea derivative as a herbicide

The present invention relates to the use of a phenylurea derivative as a selective herbicide in cereal crops.

It is known that N- (3-chloro- ⁱ ! - methoxyphenyl) -N ¹ , N ¹ -dimethylurea can be used as a selective herbicide in cereals and other crops (cf. Swiss patent specification K66 94j5). However, its effect is bad.

It is known that N- (3-chloro-4-methoxy-phenyl) -N'-methyl-N ¹ -methoxy-urea has strong herbicidal properties (US Pat. No. 5,228,762), albeit chemical and biological Properties of this compound are not described in more detail in the cited patent. This active ingredient is claimed to combat the monocotyledonous Cyperaceae, which are difficult to control with chemicals, and as a selective herbicide in the resistant crops of maize, sugar cane, sorghum and soy.

It was found that the N- (j5-chloro-4-methoxy-phenyl) -N'-methyl-N ^f -methoxy-urea

in addition to the well-known herbicidal properties, a very excellent one Has selectivity in cereal crops. It is surprising that this urea derivative has a very high tolerance in the monocotyledonous and chemical-sensitive types of grain (barley, rye, wheat, oats), without that safe weed killing must be dispensed with. Under weeds are such plants (grasses or herbs) to understand commonly used in cereals as competitors

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occur in the crop. The tenant had at the use of N-i ^ -Chlor - ^ - methoxy-phenylJ-N'-methyl-N'-methoxyurea as a selective grain herbicide to overcome a great technical prejudice because it must seem pointless to use one Substance that is able to kill the extremely robust "nütsedge", can also be used in sensitive cereal crops without damaging them.

The active ingredient can be used as such or in the form of the usual formulations, e.g. B. as emulsifiable Concentrate, wettable powder, paste, soluble powder, dust or granules. The forms of application depend entirely according to the purposes of use; they should ensure a fine distribution of the active substance in each case.

For the production of directly sprayable solutions, hydrocarbons with boiling points higher than 150 ⁰ C, z. B. tetrahydronaphthalene or alkylated naphthalenes, or organic liquids with boiling points higher than 150 ° C and one or more functional groups, e.g. B. the keto group, the ether group, the ester group or the amide group, this group being a substituent on a hydrocarbon chain or being part of a heterocyclic ring, can be used as spray liquids.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders) by adding Water to be prepared. To produce emulsions, the substances can be used as such or dissolved in a solvent, by means of wetting or dispersing agents, e.g. B. Polyethylene oxide addition products in water or organic solvents be homogenized. But it can also consist of an active substance, emulsifying or dispersing agent and possibly a solvent Concentrates are prepared that are suitable for dilution with water.

Dusts can be produced by mixing or grinding together the active substances with a solid carrier, e.g. B. kieselguhr, talc, clay or fertilizers can be produced.

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An addition of insecticides, fungicides, and bactericides other herbicides is just as possible as the mixture with fertilizers.

The following test information explains the production of the active ingredient:

example 1

To a mixture of 90 parts (parts by weight) of N-methylhydroxylamine hydrochloride in 400 parts of water and 600 parts of methylene chloride, 40 parts of sodium hydroxide dissolved in 100 parts of water are added dropwise ^{at 5 to 10 ° C. with stirring.} 184 parts of 3-chloro-4-methoxyphenyl isoeyanate, dissolved in 100 parts of methylene chloride, are then added dropwise at 10 to 15 ° C. After stirring for three hours at room temperature, the precipitate formed is filtered off with suction, washed with water and dried. 210 parts of N- (3-chloro-4-methoxyphenyl) -N ¹ -methyl-N ¹ -hydroxyurea with a melting point of ^{0 are obtained}

107 parts of the N- (3-chloro-4-methoxyphenyl) -N'-methyl-N'-hydroxyurea obtained in this way are suspended in 540 parts of water and treated with 53.5 parts of sodium hydroxide, dissolved in parts of water, in transferred the sodium salt. 123 parts of dimethyl sulfate are added dropwise to the aqueous solution of this sodium salt at room temperature. After stirring for 12 hours, the precipitate formed is filtered off with suction, washed with water and dried. 104 parts of N- (3-chloro-4-methoxy-phenyl) -N'-methyl-N ¹ -methoxy-urea with a melting point of 95 ° C. are obtained.

The selective herbicidal action of the active ingredient can be seen from the examples below. It is especially important good tolerance in grain. Even large weeds are destroyed by high application rates, those of the grain still without significant damage can be tolerated. There is real selectivity here.

The active ingredient can be used both before and after emergence of the crop plants.

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Example 2 -

The plants wheat (Triticum aestivum), barley (Hordeum vulgare), white goosefoot (Chenopodium album), real chamomile (Matricaria chamomilla), mustard (Sinapis arvensis), amaranth (Alopecurus myosuroides), annual bluegrass (Poa annuaa) and barnacle millet crus-galli) were grown in the greenhouse at a height of 3 to 17 cm with 2 kg / ha of active ingredient II N- (3-chloro-4-methoxyphenyl) -N'-methyl-N ¹ -methoxyurea and, for comparison, with 2 kg / ha of active ingredient I N- (3-chloro-4-methoxyphenyl) -N ¹ , N ¹ 'dimethyl urea, each dispersed in 500 liters of water per ha, treated. After 2 to 3 weeks it was found that the active ingredient II showed a better selectivity on the crop plants and an equally good effect on weeds and grass weeds as I did.

The result can be seen from the following table:

Active ingredient I. II 35 10 35 10 100 100 100 100 100 100 100 100 95 95 90 90

Triticum aestivum Hordeum vulgar

Chenopodium album Matricaria chamomilla Sinapis arvensis Alopecurus myosuroides poa annua
Echinochloa crus-galli

0 = no damage 100 = total damage.

Example 3

In the greenhouse, clay-containing sandy soil was poured into test pots and the seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), annual bluegrass (Poa annua), amaranth (Alopecurus myosuroides), chicken millet (Echinochloa crus-galli),

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white goosefoot (Chenopodium album) and field mustard (Sinapis arvensis). The soil prepared in this way was then treated with 2 kg / ha of active ingredient II N- (3-chloro-4-methoxyphenyl) -N'-methyl-N'-methoxydurea and in comparison with 2 ieg / ha active ingredient I N- (3-chloro-4-methoxyphenyl) -N ', N'-dimethyl urea, each dispersed in 500 liters of water per hectare, treated. After a test period of 4 to 5 weeks it was found that II showed a better tolerance than I on the useful plants, with equally good herbicidal action on undesirable Plants.

The test result can be seen from the following table:

Active ingredient I. II Useful plants: 15th Triticum aestivum 0 20th Hordeum vulgar 10 Unwanted plants: 100 Poa annua 100 95 Alopecurus myosuroides 100 95 Echinochloa crus-galli 95 100 Chenopodium album 100 100 Sinapis arvensis 100

0 = without damage
100 = total damage.

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Claims (1)

- β - O.Z. 27 881 Claim Use of the compound of the formula ΓΉ 3 "v ^ y" ^ och, Cl ^ for selective weed control in cereal crops. Badische Anilin- & Soda-Fabrik AG Ju // 3 nights 9 8 2 G / 1 1 2 2