DE1642215B - Means for inhibiting plant growth and for changing the plant habitus - Google Patents

Description

R ₁

-C ₆ H ₁₂ -NR ₃

R ₁ -NR ₃ Y «

where R ₁ and R _{2 are} an alkyl radical or R ₁ and R ₂ together are an alkylene radical, R _{3 is} an ethyl radical or propyl radical optionally substituted by chlorine or hydroxyl, R _{4 is} the radical

-C ₆ H ₁₂ -NR ₃

or R ₃ and R ₄ together represent the remainder

-C ₄ H ₈ -NC ₄ H ₈ -

R,

or

or R ₃ and R ₄ together represent the remainder

R ₁
-C ₄ H ₈ -NC ₄ H ₈ -

or

R ₁ -C ₂ H ₄ -NC ₂ H ₄ -

or together with the nitrogen whose substituents they are, the remainder of morpholine or 2,6-dimethylmorpholine or thiomorpholine, where R ₁ , R ₂ and R _{3 have} the meanings given above, Y is an anion and η is 1 or 2 .

2. Agent according to claim 1, characterized by a content of Ν, Ν-dimetnylmorpholinium chloride.

It is known to use chlorcholine chloride (CCC) to inhibit the growth in length in wheat plants. It is also known that N-dimethyltminosuccinamic acid (A) can be used to inhibit the growth in length of λ'οη tomatoes. However, their effects are unsatisfactory.

It has been found that compounds of the formula

R ₁ -NR, Y _n

where R ₁ and R _{2 are} an alkyl resl or R ₁ and R ₂ form —C ₂ H ₄ —N — C ₂ H ₄

R ₂

or together with the nitrogen whose substituents they are, the remainder of the morpholine or 2,6-dimethylmorpholine or thiomorpholine, where R ₁ , R ₂ and R _{3 have} the abovementioned meaning

tungen have, Y is an anion and η denotes the numbers 1 or 2, are suitable for inhibiting the growth in length in plants. The treated plants have a stocky habit. A darker leaf color can also be observed.

The agents according to the invention can, for example, sprayed onto the leaves or the ground, into the Incorporated into the soil or used to treat the seeds. The effect is mainly due to the cation

conditionally, so that Y is, for example, chloride, bromide, p-toluenesulfonate, V ₂ may mean sulphate or ^1/3 phosphate any anion. The meaning of η depends on how many quaternary nitrogen atoms are present in the cation.

The active ingredients can be produced, for example, as follows:

The morpholine or piperazine is used with alkylating agents, e.g. B. alkyl halides or alkyl sulfates. Or water is split off from N-alkyl- N, N-di- (2-hydroxyalkyl) amines, for example by the action of concentrated sulfuric acid, and the morpholine derivative thus obtained is alkylated, for example with alkyl halide, to give the corresponding quaternary compound. Also by implementing

(10 2,2'-dichlorodialkyl ethers with alkylamines in the presence Acid-binding agents can be obtained from the morpholine rivals, which can then be reacted with alkylating agents. z. B. alkyl halides, weiden alkylated to the corresponding quaternary compound.

f> 5 The active ingredients can also be manufactured by reacting an aliphatic secondary monoamine or a saturated nitrogen-containing one heterocyclic compound (e.g. piperidine or his

Homologues) with a dihaloalkyl compound. In the case of these monoamines, alkylation to the tertiary amine takes place in the first stage and further alkylation to give the corresponding quaternary compound in the second stage. ^{Tertiary 5 Cl 0} diamines, in which reaction with dihaloalkyl compounds results in the alkylation to give the corresponding quaternary compounds, can also be used as starting materials. In this case, one nitrogen atom or both nitrogen atoms of the diamine can be converted into the quaternary form. For example, by reacting tetramethylethylenediamine with 1,2-dichloroethane, a compound of the following formula is obtained

butane is a compound represented by the following formula

CH ₃ CH ₂ CH ₂ CH ₂ CH ₂ CH ₃

N N

CH ₃ CH ₂ CH ₂ CH ₂ CH ₂ CH ₃

CH ₃ CH ₂ -CH ₂ CH ₃

CH ₃ CH ₂ -CH ₂ CH ₃

Cl ⁶

20th

and from 2 moles of dimethylamine and 2 moles of 1,4-dichloro-Das the following example explains the manufacturing process:

990 parts (by weight) of hexamethyleneimine are heated in a heatable stirred vessel at 130 ⁰ C. Then 318 parts of 1,4-dichlorobutane are pumped in uniformly over the course of 2 hours and the mixture is kept at 130 ° C. for 1 hour.

The reaction mixture is treated with a methanolic solution containing 30 percent by weight of sodium methylate contains, neutralized, of the precipitated common salt by filtration and of the excess methanol and hexamethyleneimine freed by distillation. The crystallized one is obtained from the residue Quaternary salt by recrystallization from acetonitrile in good yield. The connection has the following Constitutional formula:

Cl ^e

\ ^ Γΐ2 wrl2 CH2 CH2 C ** 2 C "2 C02 CH2 CH-2 ί— Η.2

(_ri2 Crl2 CH2 C02 ^ * ^ 2 C02 Cri2 C02 CH.2 v- * l2

The following are examples of the active ingredients:

R ₁ -NR ₃ Yj?

R ₁ R ₂ R ₃ R ₄ —C ₂ H _4. —O — C ₂ H ₄ CH ₃ θ
^ -C ₄ H ₈ - C _n H ₁₂ -C ₂ H ₄ Y η 1.554 Il -CH ₃ -CH ₃ C ₂ H ₄ Cl - C ₆ H ₁₂ N® <C ₄ H ₈ C ₄ H ₈ 1 CH,
■ Cl 1 1.543 III C ₄ H ₈ C ₂ H ₄ Cl CH, Cl 2 ■ -C ₂ H ₄ -I Nf-CH ₄ - 1.530 IV CH ₃ CH ₃ CH ₃ Cl 2 -C ₄ H ₈ -N- O ₁ H ₁₂ -C ₄ IV- -C ₂ Hr-N- 1,635 V - CH ₃ -CH ₃ Cl ") 1,538 Vl - C ₁₁ H ₁₂ Cl 1 1,540 VI ■ - L ₁ , Cl 2

continuation

R ₄

VIII

C ₂ H ₅ C ₂ H ₅

-C ₂ H ₄ -NC ₂ H ₄ -

Cl

1,550

IX

-C ₄ H _{9 C 4 H 9}

-QH ₄ -N

-C ₂ H ₄ -

Cl

1.528

The agents according to the invention for influencing plant growth can be used as solutions, emulsions, Suspensions or dusts are used. The forms of application depend entirely according to the purposes of use; they should in each case a fine distribution of the active substance guarantee.

For the preparation of directly sprayable solutions, the solution is in water, if necessary with the addition of wetting agents. But it can also be hydrocarbons, such as tetrahydronaphthalene, and alkylated naphthalenes can be used as spray liquids.

Dusts can be produced by mixing or grinding the active substances with them a solid carrier. The effect of the funds can be increased by adding Plant protection products are to be broadened.

The active ingredients can also be in the form of a mixture with fertilizers, for example in the form of Fertilizers, in which the active ingredients are incorporated, are used.

The following examples explain the action of the agents according to the invention.

example 1

Wheat grains of the "Heines Koga" variety were placed in glass vessels with a diameter of 11.5 cm (New building shells) in a loamy sandy soil that was previously adequately supplied with nutrients, sown. On the day of sowing, the active ingredients were sprayed onto the surface of the soil in Quantities of 3 mg / shell each corresponding to 3 kg / ha. After 4 weeks the following results were found:

Influencing the length growth of wheat (soil treatment in Neubauer trays)

Active ingredient

Attempt 1

Control (untreated).

CCC

II

IV

Attempt 2

Control (untreated)

CCC

II

Plant height in cm relative

21.2 15.0 12.5 13.3

19.5 14.7 14.1

100 70.8 59.0 62.7

100

Active ingredient III has the same effect as II and IV.

Example 2

Under the same conditions as in Example 1, but with different application rates of the active ingredients, four trials were carried out with spring barley (variety »Breuns Wisa«). After 4 weeks were found the following results:

Influence of the growth in length of spring barley through soil treatment (Experiments in new building shells)

Active ingredient

Attempt 1
Control (untreated).

CCC

CCC

II

II

Attempt 2

Control (untreated).

CCC

Il

IV

in cm Plant height relative Application rate 31.4 100 Ul 99.0 30.4 96.8 3 kg / ha 27.4 87.3 12 kg / ha 25.3 80.6 3 kg / ha 20.9 100 12 kg / ha 17.4 83.3 15.5 74.2 12 kg / ha 16.5 78.9 12 kg / ha 12 kg / ha

Active ingredient

Attempt 3

Control (untreated).
I.

Attempt 4
Control (untreated).

CCC

II

continuation

Aulwandmenu

12 kg / ha 12 kg / ha 12 kg / ha

3 kg / ha 3 kg / ha

S '

Plant height

20.5
17.7
16.0
16.9

21.0
16.2
15.4

relative

100 86.3 78.0 82.4

100 77.1 73.3

The same biological effect as II and IV also show the following active ingredients: III.VIII, VII, VI and V.

Example 3

Barley plants of the “Breuns Wisa” variety were treated with the active ingredients at a height of about 10 cm sprayed in the usual way (application rate 2 kg active ingredient / ha). The effect of the over the sheet added substances can be seen from the following results:

Influence of growth in length of spring barley with leaf treatment

(Experiment in new building shells)

Active ingredient

Control (untreated)

CCC

II

Example 4

Plant height in cm relative

30.1 29.8 26.9

100 99.0 89.4

In order to determine the effect of the treatment with the various active ingredients on spring barley until the plants were fully ripe, a test was carried out in the usual way in Mitscherlich containers (spraying of the active ingredients on the leaves of the plants; application rate 3 kg active ingredient / ha). A neutral loamy sandy soil was used (fertilization with 1 g of N as ammonium nitrate and 1 g of P ₂ O ₅ as secondary potassium phosphate per vessel). The following numbers indicate the rooster length of the ready-to-harvest plants:

Influence of the cock length of spring barley through leaf treatment (experiment in Mitscherlich vessels)

Active ingredient

Control (untreated)

CCC

II

Plant height in at relative

82.8 83.3 77.1

100 100.6 93.1

Example 5

Under the same conditions as in Example 4, a test was carried out with summer rye of the variety "Petkus" carried out in Mitscherlich vessels, which had the following results:

Influence the length of the stalk of summer rye

for leaf treatment (experiment in Mitscherlich vessels)

Active ingredient

Control (untreated)

CCC, 3 kg / ha

IV, 3 kg / ha

Plant height in cm relative

154.5 141.4 135.5

100 91.5

87.7

Example 6

Tomato plants of the cultivar “M / M” were grown in a greenhouse experiment in customary plant pots at a height of about 12 cm with N-dimethylaminosuccinamic acid (A) and another active ingredient both via the soil and via the leaf with different application rates of the active ingredients treated. Four weeks after the treatment, the length measurement became the following values determined.

Influence of the length growth of tomatoes through soil and leaf treatment (Greenhouse experiment in plant pots)

5 mg .. Plant height relative 15 mg .. in cm 100 55 control (untreated) 30 mg .. 30Y Active ingredient A 5 mg .. 96.4 Soil treatment with 29.1 97.0 Soil treatment with 5 mg .. 293 818 ⁶⁰ soil treatment with 15 mg .. 25.0 69.5 Leaf treatment with 30 mg .. 2K0 Active ingredient II 5 mg .. 89.1 Soil treatment with 26.9 83.8 Soil treatment with 25.3 67.2 Soil treatment with 20.3 71.5 Leaf treatment with 21.6

209537/5

2548

Claims (1)

Patent claims: 1. Means for inhibiting the growth of peacocks and for changing the plant habit, characterized by a content of a compound of the formula together an alkylene radical, R ₃ an ethyl or propyl radical optionally substituted by chlorine or hydroxyl, R ₄ the radical