DE1542830A1 - Means to inhibit the growth in length and to influence the plant habit - Google Patents

Description

BADIoumi AiMiJjiJM- & SODA-PABrIK AG

Our reference: O.Z. 24 334 Sehs / Gn "Ludwigshafen am Rhein, July 6th, 1966

Means for inhibiting the growth in length and for influencing the plant habit

It is known that the stability of wheat is caused by treatment with chlorcholine chloride (CCC) and the result Shortening the length of the stalk and increasing the diameter of the stalk. However, there is a risk that the wheat is damaged by this substance.

It has been found that compounds of the formula

R - N * - R ₀

R ₃

in which IL, Rp and R, each a methyl radical and R. a methyl radical substituted by chlorine or an optionally substituted by chlorine aliphatic radical with 4 carbon atoms or the isopropenyl or trichloroallyl radical or R ₁ and R ₂ a methyl or ethyl radical and R is an ethyl radical and R. is an optionally substituted by chlorine aliphatic radical having 2 to 3 carbon atoms and X is an anion, a strong inhibition of the

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Plant growth ". The plants exhibit one stocky habit. A darker leaf color can also be observed.

Since the biological action of the compounds is caused by the cation, X can be any anion. Preferred are chloride, bromide, hydroxide, methosulphate, ethyl sulphate, Hydrogen sulfate or p-toluene sulfonate.

The products according to the invention can be produced by various synthetic routes, for example:

1) Alkylation of tertiary amines with alkyl halides or Alkyl sulfates using known methods, e.g. in acetonitrile?

Acetonitrile

CH, ^
C ₂ H ₅ -N + CCl ₂ = C y _ CH ₂ -CJ = CC1 ₂ CH ₂ Cl CH ₃ ^ * Cl Cl " ^CH 3 \»
C ₂ H ₅ -N- Cl CH ₃ ^

2) Alkylene oxide addition to lower tertiary aliphatic amines to form quaternary hydroxylalkylanunonium salts, the again converted into the haloalkylammonium salts with hydrogen halide under pressure or with thionyl chloride

can be:

-3 «

Q09823 / 1842

GH,

(CH,), N + CHo-C-CH

^{5 5} <ο "

3 + H

0.Z. 24 334

- C - OH

C.
CH,

+ HCl

CH,

- CH,

- hi

Cl

3) Implementation of tertiary amines with substituted
1,2-dihaloalkanes, e.g. 1,2-dichloropropane:

in acetonitrile

Cl Cl

-HCl

- C

CH

3 -I

Cl

Γ * Ί

(CH ₃ ) ^ NH

71

4) Another possibility for the production of the products according to the invention consists in the implementation of Tono ^ uKDihalogenalkanen in anhydrous solvents, where the «^ -dihalogenalkane itself can be used as such (excess), for example:
(CH ₃ ) ₃ N + Cl - GH ₂ - Gl »[(CH 1 N - CH ₂ Cl] Cl

To illustrate the synthesis methods described above, the following preparation example is given:

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1) NtN-trimethyl-N-carbonomethylammonium chloride ; In a corrosion-resistant autoclave 425 parts by weight of methyl chloride and 15 parts by weight of trimethylamine are heated for 5 hours at 13O ⁰ C. That. The product obtained in this way is recrystallized from a large amount of acetone or ethyl acetate. A reaction product of methylene chloride which is only converted on one side is obtained, namely NjNjN-trimethyl-lf-chloromethylammonium chloride; Mp. 162 to 164 ⁰ O.

For the physico-chemical characterization of the invention Substances are listed below, some melting points, as the majority of the compounds specified here has not yet been described in the literature:

N, N-dimethyl-H-ethyl-Ii- (2-chlorallyl) ammonium chloride

Mp 114 to 115 ^° C

N, N, N-trimethyl-IT- (ß-methyl-ß-chloro-n-propyl) -ammonium i od id

M.p. 162 to 164 ^° C

N, H, N-trimethyl-H- (et-methylpropinyl) ammonium chloride

Mp 225 to 226 ^° C

ff, H, H-trimethyl-ff- (2,5 ♦ 3-trichlorallyl) ammonium chloride

Fp 2 '

Ν, Ιί-dimethyl-N-ethyl-N-allylammonium bromide

Fp ί

H, N-dimethyl-5-ethyl-N- (2-ohiorethyl) ammonium bromide

H, N-dimethyl-H, N-diethylammonium bromide

Mp 215 ⁰ C 216 bie

Fp 58 to 59 ⁰ C

Mp 112 ⁰ C.

Fp 321 tie 322 ⁰ C

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Ν, Ιϊ-dimethyl-N-ethyl-If-iBopropylammoniumbromid If, N, N-triethyl-N-methylammonium bromide

NjNjir-trimethyl-N-isopropenylammonium chloride

Pp 273

N, Ä, Ν-Trimethyl-N-methyl-cyclopropylaiimoniumehlorid

Pp 287 ⁰ G

Pp 295 to 296 ⁰ C

Pp 273 to 274 ⁰ C

Pp 178 to 180 ^° C

The solubility of the products according to the invention, e.g. in water, which is mainly used as a solvent is imprinted can generally be described as good to very good and thus does not present any application difficulties.

The agents according to the invention can be used as solutions, emulsions, suspensions or dusts. The application forms depend entirely on the purposes of use; they are supposed to provide a fine distribution of the effective in each pail Ensure substance.

For the production of directly sprayable solutions comes the solution in water into consideration. But it can also be hydrocarbons, such as tetrahydronaphthalene, and alkylated naphthalenes can be used as spray liquids.

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Aqueous use forms can be added from emulsion concentrates, pastes or wettable powders (wettable powders) be prepared by water. To produce emulsions, the substances can be used as such or in a solvent dissolved, homogenized by means of wetting or dispersing agents in water or organic solvents. It can but also concentrates consisting of active substances, emulsifiers or dispersants and possibly solvents which are suitable for dilution with water.

Dusts can be produced by mixing or grinding together of the active substances made with a solid carrier will. The active substances can also be mixed with fertilizers.

The agents according to the invention can on the one hand on the Soil, but on the other hand, can also be supplied as a spray treatment via the leaf. There is still the possibility of seed treatment.

The effect of the compounds according to the invention is based on the the following test results:

Young wheat plants of the variety were grown in new building pans "Friesdorfer Opal" on a loamy sandy soil with additional Nutrient enrichment with a complete fertilizer 13/13/21

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(50 mg N / shell) attracted. At a height of 7 to 9 cm the first spray treatment with 15 * strength aqueous solutions of the Connections to be tested. Bach, this treatment was repeated for two weeks. Finally, 4 days later, the last treatment with 2.53 * solutions. The respectively supplied Amounts of active ingredients and the frequency of treatment correspond to the conditions of a load test. Three Weeks after the first treatment, on the one hand, the height of the plants and, on the other hand, that due to the supply of active ingredients. caused damage checked. Based on that international scheme for assessing the herbicidal effect was based on a ten scale (1 = no damage and 10 = total loss) rated.

Active ingredient Wuohshöhe damage

the degree of plants in cm

Control (untreated) chloroholine chloride (CCC)

N, N, N-trimethyl-F-chloromethylammonium chloride

N, N, N-trimethyl-ff-Cß-chloro-ß-ethylpropyl) ammonium iodide

N, N, N-Trime thy 1-H - («t-methyl-propyn-1-yl-3) -ammonium chloride N, N, N-trimethyl- (2,3,3-trichloroallylammonium chloride)

N, N-dimethyl-ir-ethyl-ir- (fl-chloroethyl) ammonium chloride

N, N, N-triethyl-N-methyl-awiottium bromide

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42.5 1 until 2 22.5 4th 27.5 1 until 2 30.5 2 until 2 28.0 1 31.0 T 27.5 1 27.5 1

OZ ₀ 24 334

Active ingredient

Height of stature of plants in cm

Degree of damage

N, N, N, N-tetraethylammonium tromide 29.5 N, N-I) imethyl-N, N-diethyl-ammonium-

bromide 30.0

N, N-dimethyl-N-ethyl-N-allylammonium chloride 31.5

N, N-dimethyl-N-ethyl-N- (ß-chloro-

allyl) ammonium chloride 31.5

1 to 2

1 to 2

As can be seen from the cited test results, have the agents according to the invention cause a similarly strong reduction in stature height as the standard substance CCC; she however, showed significantly less damage to the plants or the leaves.

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Claims (1)

Z. Agent for inhibiting plant growth and influencing the plant habit, containing a compound of the formula _π 1
I » ~ ^R e · in which B., R ₉ and B ^ each have a methyl radical and R _{4 is} a methyl radical substituted by chlorine or an aliphatic radical with 4 carbon atoms that is optionally substituted by chlorine or the isopropenyl or the triehloral.lyl radical or R ₁ and R _? a methyl or ethyl radical and R ₅ an ethyl acetate and R. an aliphatic radical optionally substituted by chlorine with 2 to 3 carbon * cost and X tin anion, 1 BADISCHE ANIIIN & SODA FACTORY A BJ 009823/1842