DE1919975A1 - Urea derivatives - Google Patents

Description

Badische Anilin- & Soda-Fabrik AG

Our reference: O.Z. 26 149 B / B 67OO Ludwigshafen, April 18, 1969

Urea derivatives

The invention relates to new valuable urea derivatives and herbicides, which contain these compounds.

It is known to use trisubstituted ureas, e.g. N-p-chlorophenyl-N'-methyl-N'-methoxyurea, to be used as herbicidal agents.

These funds are particularly useful when used in the wet-on-bake method not always a satisfactory tolerance to cultivated plants.

It has now been found that urea derivatives of the formula

CH,
NH-CN ^ ■>

in which R is an unsaturated aliphatic radical (allyl, propargyl, Butyn- (1) -yl- (3), butyn- (2) -yl- (3), 3-methyl-butyn- (l) -yl- (3)) and R, a saturated or unsaturated aliphatic radical (methyl, ethyl, propyl, butyl, allyl, propargyl) means a show good herbicidal activity and crop plant tolerance.

The active ingredients can e.g. be produced in a two-step synthesis will. In a first stage, an aminophenol is used with a carbamic acid halide of the formula

X-C-N

0 ^OR 1

to, in which X is halogen and R ₁ has the meanings given above, to the corresponding N-hydroxyphenylurea, which is in a

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second stage is alkylated with a suitable alkylating agent.

The preparation of the compounds according to the invention is illustrated by the following information:

1st stage

Production of N-methyl-N-methoxy-N'-3-hydroxypheny! Urea

To a solution of 654 parts by weight of m-aminophenol in 2800 parts by weight of tetrahydrofuran, 372 parts by weight of N-methyl-N-methoxycarbamic acid chloride were added dropwise at 25 ° to 55 ° C. with stirring. After stirring for three hours at 20 ^° C., the precipitated hydrochloride was filtered off with suction. The filtrate was concentrated in vacuo, the residue was treated with water and, after suctioning off, ^{dried at 50 °} C. in vacuo; Yield: 530 parts by weight, m.p.

. 2nd stage

Manufacture of N-methyl-N-methoxy-N * -3- (propargyloxy) -phenylurea

-CH ₂ -CeCH

A mixture of 392 parts by weight of N-methyl-N-methoxy-N'-3-hydroxy. pheny! urea, 28o parts by weight of anhydrous potassium carbonate and 250 parts by weight of propargyl bromide (95 percent) in 2000 parts by weight of aoetone was refluxed for 13 hours. After cooling down was separated from the salt, and the piltrate was concentrated in vacuo

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and the residue crystallized from Benzo1 / cyclohexane recrystallised: mp 64 to 66 ⁰ C..

In a corresponding manner, one obtained
N-methyl-N-methoxy-N ^ -CallyloxyJ-phenylurea m.p. 59 to 61 ° C.

The herbicides according to the invention can be used as solutions, emulsions, Suspensions or dusts are used. The forms of application depend entirely on the intended use ensure a fine distribution of the active substance in each case.

Hydrocarbons, such as tetrahydronaphthalene, and alkylated naphthalenes 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 prepare emulsions the substandard _may% zen as such or dissolved in a solvent, can be homogenized by means of wetting or dispersing agents in water or organic solvents. However, concentrates which are suitable for dilution with water can also be prepared from active substances, emulsifiers or dispersants and possibly solvents.

Dusts can be produced by mixing or grinding the active substances can be produced with a solid carrier.

example 1

The plants Oryza sativa, TritJ.cum vulgare, Sinapis arvensis, Chenopodium album, Urtica urens, Stellaria media, Poa annua and Panicum crus-galli were treated with N-methyl-N-methoxy-N'- at a height of 2 to 15 cm. J-ipropargyloxyJ-phenylurea (l), N-methyl-N-methoxy-N ^f -3- (allyloxy) -phenylurea (il) and in comparison with N-methyl-N-methoxy-N ^l -4-chloropheny! urea (III) treated. The application rates were each 1.5 kg of active ingredient

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Hectares dispersed in 500 liters of water per hectare.

The test after J5 to 4 weeks showed that the 'active ingredients I and II compared to III showed a better selectivity on Oryza sativa and Triticum vulgare with about the same good herbicidal effect,

The test result can be found in the following table:

Active ingredient

II

III

Oryza sativa 10-20 10 30-40 Triticum vulgar 10 10 30th Sinapis arvensis 90-100 90-100 90-100 Chenopodium album 90-100 90-100 90-100 tlrtica urens 90-100 90-100 90-100 Stellaria media 90-100 90-100 90-100 Poa annua 90-100 90 90 Panicum crus-galli 90 80-90 90 0 = no effect 100 = total effect Example 2

Bowls of 20 χ 20 cm were filled with loamy sand soil and with the seeds of Sinapis arvensis, Chenopodium album, Lamium amplexicaule, Poa annua, Panicum crus-galli, Oryza sativa and Triticum vulgare and then sown with N-methyl-N-methoxy-N'-j5- (allyloxy) -phenylurea or with N-methyl-N-methoxy-N'-J-Cpropargyloxy -) - phenylurea treated, the active ingredients in an amount of 2 kg per hectare dispersed in 500 liters of water were applied per hectare.

After 4 to 5 weeks it was found that the plants Sinapis arvensis, Chenopodium album, Lamium aplexicaule, Poa annua and Panicum crus-galli were nearly dead, while Oryza sativa

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and Triticum vulgar in both products with almost no damage weiterervfuchsen.

-6-00984S / 1897

Claims (4)

-6- OZ 2β claims 1Λ urea derivative of the formula CH »I. RO 0 in which R is an unsaturated aliphatic radical and R «is one means saturated or unsaturated aliphatic radical. 2. Herbicide, consisting of or containing a compound as characterized in claim 1. J5. N-methyl-N-methoxy-N ¹ -3- (allyloxy) -phenyl! Urea. 4. N-methyl-N-methoxy-N ¹ -3- (propargyloxy) phenyl urea. Badische Anilin- & Soda-Fabrik AG ₁ 009845/1887