CS236690B2 - Plant growth regulating agent - Google Patents

Abstract

- The plant growth regulator according to the invention contains as active ingredient a compound of the general formula I Ri Cl ■ \ | N—C—C-H (I) - / II I ■ r2 o ci in which Ri and R2 have the meaning given in the description in an amount of 5 to 80% by weight, 10 to 95% by weight of at least one solid and/or liquid carrier and 0.5 to 15% by weight of at least one surfactant. By treating plants using the composition according to the invention, it is possible to stimulate plant growth and significantly increase the fresh weight of plants

Description

The invention relates to a plant growth regulator which contains substituted halocarboxylic acid amides as an active ingredient.

A wide range of compounds capable of regulating plant growth is known from the literature. One group of these compounds — called regulators — consists of natural or synthetic hormones [Kólcsei M., Nádasy M.: Magyar Kémikusok Lapja 34 (3), 122—126 (1979)J. Such compounds are natural or synthetic auxins, gibberellins, cytokinins and abscisins or their synthetic analogues.

Chlorocholine chloride, which inhibits cell growth in the longitudinal direction, has been known for a long time and is widely used to strengthen cereal stalks.

According to US Patent No. 3,156,544, it is known that certain (2-haloethyl)trialkylammonium salts, especially (2-chloroethyl)trimethylammonium chloride, have an effect on plant growth and are characterized by a regulatory effect. Hungarian Patent No. 164,885 describes the germination-inhibiting effect and the longitudinal cell growth-inhibiting effect of certain pyrimidine derivatives, e.g. 2-methylthio-4-ethylamino-5-nitro-6-methylaminopyrimidine, and their salts.

According to Hungarian patent no. f 170 761, some phthalimide derivatives increase the germination and growth rate.

The inventors' experiments on plant growth regulation show that plant growth can be stimulated and the fresh weight of plants can be significantly increased by treatment with the composition according to the invention.

The plant growth regulator according to the invention contains as active ingredient a compound of the general formula I

R _t Cl \ I

N—C—C—Η (I) / II I r ₂ o Cl in which R _t and R ₂ may be the same or different and represent a hydrogen atom, a straight-chain or branched alkyl group of 1 to 4 carbon atoms, a cyclohexyl, phenyl, chlorophenyl group, a phenyl group substituted by one or two alkyl groups of 1 to 4 carbon atoms, a benzyl group, optionally substituted by an alkyl group of 1 to 4 carbon atoms, or R j and R ₂ may together form an alkylene group of 1 to 6 carbon atoms. The composition contains a compound of formula I in an amount of 5 to 80 % by weight, 10 to 95 % by weight, at least one solid and/or liquid carrier and 0.5 to 15 % by weight of at least one surfactant.

As a solid carrier, amorphous silicic acid or a silicate-type mineral can be preferably used, and as a surfactant, wetting agents and dispersants can be preferably used. Furthermore, a water-immiscible solvent such as a halogenated or aromatic hydrocarbon can be used as a carrier, and a mixture of anionic and nonionic surfactants can be used as a surfactant. Furthermore, a synthetic amorphous silicic acid or a silicate-type mineral can be preferably used as a solid carrier, and/or a synthetic fraction of mineral white oil or a water-immiscible organic solvent such as a halogenated or aromatic hydrocarbon can be used as a surfactant, and a mixture of anionic and nonionic surfactants can be used as a surfactant.

Amides of substituted halocarboxylic acids of the above general formula I are known from the literature, but their effect in stimulating plant growth is unknown.

Disubstituted amides of the above acids can be prepared by known methods [e.g. Houben-Weyl: Methoden der organischen Chemie, vol. XI/2. 3—37 (1958)]. The most widely used method is the reaction of a halogenocarboxylic acid chloride with a secondary amine. However, compounds of the general formula I can also be prepared by the reaction of a halogenocarboxylic acid with a secondary amine in the presence of phosphorus trichloride or phosphorus oxychloride or with the simultaneous introduction of phosgene (carbamoyl chloride is formed as an intermediate).

The variety of preparation procedures allows the compounds of the above general formula I to be obtained in an easy and economical manner.

The preparation of the compositions according to the invention is illustrated in the following examples, which, however, do not limit their scope.

Example

52 parts by weight of N-(dichloroacetyl)hexamethyleneimide and 2 parts by weight of phenol are introduced into a device equipped with a stirrer, and then 17 parts by weight of xylene and 19 parts by weight of methylene chloride are added. The reaction mixture is stirred until the solids dissolve, and then 10 parts by weight of a mixture of calcium salt of dodecylbenzenesulfonic acid (Atlox 4857 Bj and alkylphenolpolyoxyethylene (Atlox 3400 Bj) are added. After the surfactants have dissolved, the solution is filtered to obtain an emulsion concentrate with a concentration of 50% by weight, which can be used for spraying with water.

Example 1 and 2

In 7.5 parts by weight of water, 2.5 parts by weight of polyglycol ether (Polyglycol 1000) are dissolved, then 59 parts by weight of technical vaseline oil, 1 part by weight of amorphous silicic acid (Ultrasyl VN 3), 10 parts by weight of fatty alcohol polyglycol ether (Emulsogen M) and 20 parts by weight of N-(dichloroacetyl) hexamethyleneimide are added.

The mixture is subjected to grinding in a laboratory pearl mill with the addition of 200 g of pearls (diameter 1.5 mm) at a speed of 775 rpm and for 1.5 hours. Then the used pearls are separated on a sieve from the formed product (FW) with a concentration of 20% by weight. The product is stable for 2 hours, after 24 hours a certain amount of sediment is separated, which behaves reversibly (can be dispersed by shaking).

Example 3

52 parts by weight of technical N-(dichloroacetyl)hexamethyleneimide, 38 parts by weight of amorphous silicic acid (Ultrasyn VN 3), 3.5 parts by weight of cresol and formaldehyde precondensate (Dispergiermittel Hoe 1494), 1.5 parts by weight of sodium salt of aliphatic sulfonic acid (Netzer IS) and 5 parts by weight of powdered waste sulfite liquor are mixed and the mixture is ground in an Alpíne 100 LU type mill.

The product prepared in this way in the form of a wettable powder (WP) contains 50% by weight of the active substance and shows a flotation ability (at a concentration of 1% by weight in water) of 91.98% and a wet residue on the screen (45 µm screen) of 9.69%.

Example 4

In an Ultraplex laboratory disc mill, 5 parts by weight of N-(dichloroacetyl)diisobutylamine and a mixture of 2 parts by weight of amorphous silicic acid, 2 parts by weight of diatomaceous earth and 1 part by weight of powdered waste sulphite liquor are ground. The ground material is homogenized together with 90 parts by weight of diatomaceous earth in a mixer for powder substances. The obtained powder product contains 5% by weight of active ingredient and has a wet residue on the sieve (100 µm sieve) of maximum 2%.

Example 5

In a laboratory mixer, 5 parts by weight of N-(dichloroacetyl)hexamethyleneimine and 70 parts by weight of vaseline oil are homogenized. While stirring, 5 parts by weight of emulsifier based on nonylphenol polyglycol ether are dissolved in 20 parts by weight of water. The mixture of active substance and vaseline oil is added dropwise and with intensive stirring to the aqueous solution of surfactant and stirring is continued for 10 minutes.

An emulsion concentrate is obtained which contains 5% by weight of active substance and is dilutable with water.

Example 6

A mixture of 80 parts by weight of N-(dichloroacetyl)cyclohexylamine, 10 parts by weight of amorphous silicic acid, 2 parts by weight of a wetting agent based on the sodium salt of alkylsulfonic acid, 3 parts by weight of a dispersing agent based on a condensate of cresol and formaldehyde and 5 parts by weight of powdered waste sulfite liquor is homogenized in a laboratory ball mill and optionally pre-ground for 1 hour. The pre-ground material is further ground to a fine form in a laboratory disc mill of the Ultraplex type with uniform addition.

A wettable powder is obtained which contains 80% by weight of the active ingredient.

Flotation ability (at 1% concentration) 86.4%, wet residue on mesh (50 µm sieve) 3.8%.

Example 7 ' ^J

In 30 parts by weight of dichloromethane, 10 parts by weight of N-(dichloroacetyl) benzylamine are dissolved with stirring and then 1 part by weight of a wetting agent based on polyoxyethylene sorbitan monolaurate is added. This solution is then sprayed onto 89 parts by weight of a granular carrier based on calcined diatomaceous earth, which is placed on a vibrating screen, under vibration. The solvent is evaporated at a temperature of 50 °C in a drying cabinet and the granular material is dried to constant weight. It contains 10% by weight of the active ingredient and the grain size is 0.2 to 1.0 mm.

Example 8

50 parts by weight of N-(dichloroacetyl)-(6-ethyl-2-methyl) aniline, 40 parts by weight of amorphous silicic acid, 3.5 parts by weight of cresol-formaldehyde precondensate, 1.5 parts by weight of sodium salt of aliphatic sulfonic acid and 5 parts by weight of powdered waste sulfite liquor are mixed, then the mixture is subjected to grinding in an Alpine 100 LU mill, thereby obtaining a product in the form of a 50% (wt.) wettable powder (WPj. Example 9

By the procedure of Example 8, a product in the form of a 50% (wt.) wettable powder is obtained from 50 parts by weight of N-(dichloroacetyl)diisobutylamine.

Example 10

According to the procedure of Example 8, a product in the form of a 50% (wt.) wettable powder is prepared from 50 parts by weight of N-(dichloroacetyl)isopropylamine.

Example 11

According to the procedure of Example 8, a product in the form of a 50% (wt.) wettable powder is prepared from 50 parts by weight of N-(dichloroacetyl)cyclohexylamine.

Example 12

By the procedure of Example 8, from 50 parts by weight of N-(dichloroacetyl)benzylamine, the product is obtained in the form of a 50% (by weight) wettable powder.

Example 13

According to the procedure of Example 8, a product in the form of a 50% (wt.) wettable powder is prepared from 50 parts by weight of N-(dichloroacetyl)-(4-methylbenzyl)amine.

Example 14

According to the procedure of Example 8, a product in the form of a 50% (wt.) wettable powder is prepared from 50 parts by weight of N-(dichloroacetyl)-3-chloroaniline.

Example 15

By the procedure of Example 8, from 50 parts by weight of N-(dichloroacetyl)aniline, the product is obtained in the form of a 50% (by weight) wettable powder.

Example 16

Tests were carried out with the emulsion concentrate prepared according to Example 1 in order to influence the growth of plants belonging to the grass family (Gramineae).

The tests were carried out in a greenhouse in plastic containers with an area of 120 ^cm2 : first, 400 g of soil was weighed into each container (soil characteristics: humus content — 2.2%, nitrogen content = 0.1%, potassium oxide content = 100 mg/100 g, phosphorus pentoxide content = 60.0 mg/100 grams, soil moisture pH — 7.4, binding capacity = = 37.6).

Then, 4 g of seeds of individual plants belonging to the grass family were placed in a container and 100 g of soil was layered. The soil surface was sprayed with various amounts of the emulsion product from Example 1, which was diluted with water, and after this treatment, 200 g of soil was weighed into the individual containers. The plants were grown — with constant watering to ensure a maximum water capacity of 65% — under artificial daylight from auxiliary light sources with a 14-hour illumination period in a greenhouse at a temperature of 18 to 20 °C.

The treatment was carried out in 20 containers and repeated 4 times, while for comparison, plants were grown in other containers without treatment.

After 14 days of treatment, the above-ground part of the plants was cut off, their fresh mass was weighed and compared with the fresh mass of untreated plants.

The results of these tests are summarized in Table I.

Table I

Number Dosage during treatment Fresh mass of active substance kg/ha of plants in %

0.16 143

0.32 196

0.65 225

1.30 271

2.60 321 without treatment 100

The test results showed a very significant growth stimulation. Already at a treatment dose of 0.16 kg/ha, the fresh mass of the treated plants is 43% greater than that of the control plants, at a dose of 0.32 kg/ha it is already double and at a treatment dose of 2.60 kg/ha it exceeds three times.

Example 17

The effect of different doses of the compounds was tested on — corn (Zea mays) MVTC — 596 — millet (Panicum sp.) — sorghum (Sorghum sp.)

The seeds were then covered with 200 g of soil and treated with various doses of the active ingredient by spraying the soil. The compounds of the invention were used in the form of 50% (w/w) of the general formula I on the various test plants.

The tests were carried out in plastic containers with an area of 113 cm ² , covered with foil, into which 400 g of soil was first filled into each container (soil characteristics: humus content = 1.39% by weight, nitrogen content = 3.10 mg/100 g, pH _H2 0 = 8.2) and then the seeds of the following tested plants were placed in the containers:

seeds/container 30 seeds/container 20 seeds/container readable powder (WP). For comparison, the same test plants were grown in containers without treatment.

After spraying, the soil was watered until a water capacity of 65% was reached and

During cultivation, evaporated water was replenished according to daily weight measurements. Plants were grown under artificial daylight from auxiliary light sources with a lighting time of 16 hours and a temperature of 18 to 20 °C.

The evaluation was carried out on the 7th day after the o10 investigation by weighing the fresh mass of the cut plants and the measurement results were reported in relation to the untreated control tests and their values were expressed in %.

The results of the tests are included below in Tables 11, III _n iv.

Table II

Effect of dosage on fresh weight of corn in %

C Compound of general formula I Dosage kg active substance/ha

0.1 0.5 1.0 2.0

Fresh weight in %

1. Control test without treatment

2. N-(dichloroacetyl)-6-ethyl-2-methyl)aniline

3. N-(dichloroacetyl)diisobutylamine

4. N-(dichloroacetyl)-isopropylamine

5. N-(dichloroacetyl)cyclohexylamine

6. N-(Dichloroacetyl)hensylamine

7. N-(dichloroacetyl)-(4-methylbenzylamine).

8. N-(dichloroacetyl)-3-chloroaniline

9. N-(dichloroacetyl)aniline

10. N-(dichloroacetyl jhexamethyleneimine

4.0

100 100 100 100 100 92.1 93.2 98.4 105.6 129.8 108.8 109.5 100.1 110.6 118.0 90.8 117.2 123.8 121.7 119.3 106.2 106.8 94.9 103.0 93.7 92.6 106.8 102.9 101.8 105.8 104.2 94.9 110.7 89.3 71.7 120.2 155.2 104.1 100.8 110.8 100.5 100.2 93.5 116.9 105.8 112.3 116.8 11.8.5 120.3 125.7

Table III

Effect of dosage on fresh weight

No. Compound of general formula I

1. Control test without treatment

2. N-(dichloroacetyl)-(6-ethyl-2-methyl)aniline

3. N-(dichloroacetyl)diisobutylamine

4. N-(dichloroacetyl)isopropylamine

5. N-(dichloroacetyl)cyclohexylamine

6. N-(dichloroacetyl)hensylamine

7. N-(dichloroacetyl)-(4-methylbenzyl)amln

8. N-(dichloroacetyl]-3-chloroaniline

9. N-(dichloroacetyl janiline

10. N-{dichloroacetyl)-hexamethyleneimine

millet in % 0.1 Dosage kg of active ingredient/ha 4.0 0.5 Fresh 1.0 i weight 2.0 in % 100 100 100 100 100 222.7 240.0 210.7 237.3 226.7 225.3 217.3 197.3 260.0 229.3 233.3 186.7 197.3 233.3 230.7 224.0 260.0 249.3 201.3 197.3 166.7 192.0 269.3 209.3 210.7 217.3 216.0 190.7 197.3 229.3 246.7 202.7 188.0 224.0 177.3 209.3 250.7 250.7 257.3 249.3 201.2 215.7 235.3 270.1 270.0

IX

Table IV

Effect of dosage on fresh weight of sorghum in %

No. Compound of general formula I Dosage kg active substance/ha

1. Control test without treatment

2. N-(dichloroacetyl)-(6-ethyl-2-methyl)aniline

3. N-(dichloroacetyl)diisobutylamine

4. N-(dichloroacetyl)isopropylamine

5. N-(dichloroacetyl)cyclohexylamine

6. N-(dichloroacetyl)benzylamine

7. N-(dichloroacetyl)-(4-methylbenzylamine).

8. N-(dichloroacetyl)-3-chloroaniline

9. N-(dichloroacetyl]aniline

10. N-(dichloroacetyl)hexamethyleneimine

The above experiments have shown that some derivatives of compounds of general formula I cause a noticeable increase in plant fresh mass when treated at a dose of 0.1 kg of active substance/ha, while when treated at a dose of 1 to 4 kg of active substance/ha, the plant fresh mass increases by 10 to 110%.

Example 18

The effect of the compounds according to the invention on the yield of maize and sugar beet crops was monitored on small field experimental plots. The tests were repeated 4 times on 20 plots, each of which had an area of

0.1 0.5 1.0 2.0 4.0

Fresh weight in %

100 100 100 100 100 113.5 117.1 116.2 107.2 104.5 106.3 101.8 118.0 122.5 100.0 107.2 111.7 131.5 112.6 104.5 107.2 110.8 108.1 101.8 125.2 107.2 112.6 120.7 108.1 118.0 112.8 116.3 118.9 100.0 95.5 103.6 119.8 112.6 109.9 107.2 96.4 107.2 129.7 124.3 125.2 102.5 106.3 112.4 118.6 119.0 98 m~. At nursing was carried out double-

self-spraying with 50% (wt.) emulsion concentrate diluted with water, for corn first at the beginning of its panicle sweeping, then at full bloom, for sugar beet first at sowing and then at the time of its protection against cercospore at a dose of 6 l/ha. 300 liters of water/ha were used.

The effect of the composition according to the invention was evaluated on the basis of the amount of plant yield obtained and was compared with the amount of yield of untreated control plants.

The results obtained are contained in Tables V and VI.

Table V

Yield of raw corn kernels No. Treatment

Yield Deviation from % t/ha of control test + t/ha

Control test without N-(dichloroacetyl)hexamethyleneimine treatment

6.38

7.21

100 +0.83

113

No. Treatment

Table VI Sugar and sugar yield Found t/ha deviation- Sugarcane yield sugar mill- from t/ha and deviation- tost % control. from exams control. +t/ha

tests +t/ha

Control test without 34.52 treatment

N-(dichloroacetyl)-hexa- 44.55 methyleneimine — 16.08 5.55 — +10.03 17.00 7.57 +2.0

The tests carried out on the above-mentioned plots show that the grain yield of corn increased significantly, exceeding 10% by weight.

In sugar beet, not only did the yield increase by more than a third, but the sugar content in raw sugar beet also increased and the sugar yield that was to be achieved from an area of 1 ha improved and was 36% higher than the yield from untreated land.

Example 19

The effect of gibberellic acid and the compounds of the invention on the yield of maize and sugar beet crops was investigated on small field trials. The tests were repeated 4 times on 20 plots, each of which had an area of 98 m ^{1 2} . The compounds of the invention were used in the form and in the doses given in Example 18. Crystalline gibberellic acid was dissolved in water and applied in a 10% (w/w) concentration, at a dose of 4 l/ha. 400 l of water/ha was used.

The results obtained are shown in Tables VII and VIII.

Table VII

Yield of raw corn kernels

No. Treatment

N-(dichloroacetyl)-hexamethyleneimine

Gibberellic acid

Yield Deviation t/ha +t/ha

7.21 +0.32

6.89 —

Table VIII Sugar beet and sugar yield %

105

100

No. Treatment

Detected

Sugar beet yield sugar/ha Deviation in % +t/ha t/ha Deviation +t/ha

Gibberellic acid

N-(dichloroacetyl)-hexamethyleneimine

37.35 — 16.43 6.14 —

44.55 +7.20 17.00 7.57 +1.43

The results of the above experiments* show that the compounds of the invention increase the yield of crop plants not only in comparison with untreated controls, but also in comparison with known regulators such as gibberellic acid.

Claims (4)

SUBJECT Composition for controlling plant growth, characterized in that it contains a compound of the formula I as active substance Rj Cl \ I N - C - C - Η (I), / II I R ₂ O Cl in which R ₁ and R ₂ may be the same or different and are hydrogen, C 1 -C 4 alkyl, straight or branched chain, cyclohexyl, phenyl, chlorophenyl, phenyl substituted with one or two C 1 -C 4 alkyl groups , benzyl optionally substituted by alkyl having 1 to 4 carbon atoms, or R _t and R ₂ may together form an alkylene group having 1 to 6 carbon atoms in an amount of 5-80 wt%, 10-95 wt% of at least one pevvynalezu Joint and / or a liquid carrier and 0.5 to 15 percent by weight of at least one surfactant. 2. A composition according to claim 1, wherein the solid carrier comprises amorphous silicic acid or a silicate type mineral, and as surfactant, wetting agents and dispersing agents. 3. A composition according to claim 1, wherein the liquid carrier comprises a water-immiscible solvent such as a halogenated or aromatic hydrocarbon and the surfactant comprises a mixture of anionic and non-ionic surfactants. Composition according to claim 1, characterized in that it contains a synthetic amorphous silicic acid or a silicate-type mineral as a solid carrier and / or as a liquid carrier a synthetic mineral white oil fraction or a water-immiscible organic solvent such as a halogenated or aromatic hydrocarbon and a surfactant mixture of anionic and nonionic surfactants.