DE1172080B - Means for influencing, in particular for promoting plant growth - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Boarding school Class: A Ol η

German KL: 451-5 / 00

Number; 1172 080

File number: S 62654IV a / 451

Filing date: April 20, 1959

Opening day: June 11, 1964

The invention relates to means for promoting plant growth.

The compositions according to the invention contain at least one compound of the general formula

Cl-

O —CH-COZ

(I)

CHO

CH _S

wherein Z represents a hydroxyl, low molecular weight alkoxy or amino radical; the latter can be used if necessary be substituted by one or two low molecular weight alkyl radicals. The invention includes likewise the alkali and ammonium salts and the salts of aliphatic or cyclic amines Compounds in which Z is a hydroxyl radical. A low molecular weight residue is understood to mean a radical containing at most 4 carbon atoms. These compounds of formula I can be found in here not claimed way by condensation of 2-formyl-4-chlorophenol or one of its salts with a compound of the general formula

Means of influencing, in particular
to promote plant growth

Applicant:

Rhone-Poulenc S.A., Paris

Representative:

Dr. F. Zumstein,

Dipl.-Chem. Dr. rer. nat. E. Assmann

and Dipl.-Chem. Dr. R. Koenigsberger,

Patent Attorneys, Munich 2, Bräuhausstr. 4th

Named as inventor:

Jean Metivier, Arpajon, Seine-et-Oise

(France)

Claimed priority:

France of April 30, 1958 (764 486)

X - CH - CO - Z

CH ₃

(H)

or one of their salts. In this formula, X represents a residue of a reactive one Esters, such as a halogen atom, or the residue of a sulfuric acid or sulfonic acid ester, preferably a chlorine or bromine atom, and Z has the meaning given above. <- ■. <,. :,.,. ,, -

! It is particularly advantageous to have the reaction in the presence an alkaline condensing agent such as sodium hydroxide, potassium hydroxide or sodium carbonate, to execute. This agent can be added to the mixture of the reactants, but you can also convert the phenol into alkali metal phenolate before it is applied to the compound of the Formula II, which is used itself in the form of the alkali salt, can act. Preferably served 2-chloro (or 2-bromo) propionic acid or one of its derivatives.

It is best to work in an inorganic (water) or organic solvent (e.g. in Ethanol, benzene, toluene or other alcohols or hydrocarbons).

¹ The new acid and its derivatives show interesting phytohormonal properties. This effect is shown • in the laboratory through an acceleration of the layer formation in seedlings (growth in thickness), c proven; through the lanolin ring test with a

as paste with 1% active ingredient, through the formation of new Organs (roots), proven by the test of root formation on tomato leaves or bean stalks, through the formation of parthenocarpic fruits (no natural fertilization, therefore fruits without Kernels), detected by treating emasculated tomato flowers.

The new products can be used in all physical forms that are common to substances with phytohormonal effects, usually in the

Mixture with at least one inert diluent. You can therefore for example in the form of powders, aerosols, emulsions or solutions in organic or: inorganic media are used. In the case of aqueous emulsions, such as them used industrially or agriculturally, it is advantageous to use a wetting, dispersing or emulsifying agent of the ionic or non-ionic type, especially one from the latter group, there non-ionic compounds are insensitive to electrolytes. The emulsion is preferred manufactured in the form of an auto-emulsifiable concentrate containing the active substance dissolved in a dispersant and / or in a solvent compatible therewith, and the composition is made ready for use by simply adding water. The new connections can also mixed with synergistic products

409 599/305

to be used. The phytohormonal compounds that comprise one or more of the compounds of the invention together with an inert diluent are also part of the invention.

For the preparation of powders, inert inorganic or organic diluents, such as Limestone, kaolin, bentonite, talc, calcined magnesia, Use kieselguhr, tricalcium phosphate, sodium sulfate, cork powder, etc. as carriers. The mixture can be prepared by grinding the active substance with the inert carrier, but one can as well the carrier with a solution of the active ingredient in a volatile solvent, which is later sold will impregnate.

The preferred solutions are solutions in water or in aromatic hydrocarbons, such as toluene, xylene or mineral or vegetable oils or mixtures of these solvents.

One can also prepare emulsions or aqueous suspensions, either directly or from Powders or solutions in suitable solvents by diluting with water. About permanent emulsions to obtain, is preferably used ionic or nonionic emulsifiers or dispersants, such as B. Sulforicinate, alkyl sulfonates, quaternary ammonium derivatives or products based on polymerized ethylene oxide.

The compositions are used in a conventional manner for phytohormonal treatment.

The following examples are intended to illustrate the invention.

A. A solution made from 100 g of 2-bromopropionic acid and 134 ecm of Sn potassium hydroxide is poured into a boiling solution of 101.7 g of 2-hydroxy-5-chlorobenzaldehyde in 130 ecm of 5N potassium hydroxide solution. After treatment under reflux for 2 hours, the mixture is allowed to cool to normal temperature and acidified with 50 ecm hydrochloric acid (d = 1.19). The precipitate formed is filtered off, dried in the air and suspended in 500 ecm of water. 90 g of potassium bicarbonate are gradually added and, after stirring for 2 hours, the mixture is filtered.

The filtrate is acidified with 120 cm hydrochloric acid (rf = 1.19). The oil formed gradually crystallizes. After drying in a vacuum melting the 2 - (2 '- formyl - 4' - chloro phenoxy) - propionic acid at 101 ⁰ C. After recrystallization from benzene to obtain 26.5 g of crystals, melting at 12O ⁰ C.

example 1

5 g of 2- (2'-formyl-4'-chlorophenoxy) propionic acid are dissolved in 50 ecm of acetone and 10 g of one are added Polycondensates from ethylene oxide and oleic acid. A part of this concentrate is mixed for use with 500 to 1000 parts of water. This mixture can be used to produce parthenocarpic tomatoes Fruits are used.

Example 2

A liquid is prepared which has the following composition:

2- (2'-formyl-4'-chlorophenoxy) -

propionic acid 20 g

n-sodium hydroxide 87.5 ecm

Acetone 20 ecm

Glycerine 150 ecm

Water '. ad 1000 ecm

This is used in a ratio of 2 to 20 ecm per liter of water to treat tomatoes.

Example 3

5 g of 2- (2'formyl-4'-chlorophenoxy) propionic acid are mixed in the form of the sodium salt intimately with 95 g of sodium sulfate. The powder produced in this way can be used in the ratio of 1 to 10 g per liter of water to treat cuttings.

Comparative experiment

The 2- (2'-formyl-4'-chlorophenoxy) propionic acid according to the invention was mixed with the known 2,4-dichlorophenoxyacetic acid in the form of their sodium salt in terms of phytohormonal effectiveness. The following comparisons were made:

1. Inhibition of the growth of cucumber roots,

2. Test with the lanolin ring,

ao 3. Root formation in tomato leaves.

1. Inhibition of the growth of cucumber roots

Germinated cucumber kernels are used which have small roots of 10 ± 1 mm in length. These Cores are placed in petri dishes containing the solutions to be examined (thirty cores per bowl).

Test specimens received an amount of distilled water equal to that of the usual bowls Amount of solution (300 ecm).

The substances to be examined are in

Dissolve acetone (concentration of product 1%), and all dilutions are made with distilled water performed. Sixty kernels are used per concentration and per product.

The dishes are stored in the dark at 25 ^° C., and the extension of the roots is measured 24 hours later. The percentage elongation with respect to the test specimen is determined. '

2. Test with the lanolin ring

The active ingredient to be investigated is dissolved in lanolin or mixed with the same, so that a paste the following composition arises:

Lanolin 89 ° / ₀

"Tween 80" 10%

Active ingredient 1%

This paste is put in the form of a ring around the stems of young plants, and 10 days after After the treatment, the effects on the sprouts of the treated plants are observed. One weighs each sprout and measures its length. These two values are compared with the test specimen and the results expressed as a percentage of weight and length with respect to the test specimen.

Plants used:

Beans - When the cotyledon leaves are well developed, the sprout is about 5 mm in length. The lanolin ring is placed around the stem of the plant.
Sunflowers, cucumbers - if the cotyledons are well developed, the sprout is barely formed. The lanolin ring is around the stem

placed immediately under the cotyledons.

Twelve plants are used per active ingredient and per plant species.

3. Root formation in tomato leaves

Take the third and fourth leaves of the tomato sprout (varieto Marmande), the five to six Has leaves. The petiole of each leaf is dipped 2 to 3 cm in length into the one to be examined

Solution enclosed in a test tube (18 x 180 mm). 8 days after the start of the experiment count and measure the number of roots formed on the petioles of the treated leaves. the The results obtained are summarized in the table.

Inhibition of root
7o ver Test with the lanolin ring 7oL cucumber 7oL Sunflower 7oL >. received 26th 33 44 72 [ Root formation in tomato leaves 7o leaves number of middle
Length of
root 14th
1 O 20th Growth of length Bean 100 7oP 100 7oP 100 66 1 Conc with root in mm 13th
16
15th 24
22nd
18th Used
Active ingredient Cucumber
Conc tion 7oP 100 100 tration root per sheet 15th tration 100 100 mg / 1 20th 3 10 mg / 1 > 40 0 50 12th 6th control 0 7th 0.01 65 16 2 Acquaintance 24 0.03 20th 28 2 Active ingredient 0.3 jU
ΟΛ 0.1 10 10 received sheets (2,4-dichloro-. 0.1
Λ CYX yu 0.3 75
1 f \ T \ phenoxyacetic U ₅ Uj 19th 1 100
83
83 acid-sodium salt) υ, υι 40
95 0.03 Invention 100 0.1
0.3
1 according \
Active ingredient [ 10
1

The table shows that the compound according to the invention has a very much lower phytotoxicity and has a much better phytohormonal activity than the known comparative compound.

Claims (2)

Patent claims: 1. Means for promoting plant growth with a content of at least one phenoxycarboxylic acid derivative the general formula 40 wherein Z represents a hydroxyl, low molecular weight alkoxy or amino radical, which latter possibly by one or two low- molecular alkyl radicals may be substituted, including the alkali, ammonium and amine salts such compounds of the above formula in which Z represents a hydroxyl radical, optionally along with a diluent. 2. Means according to claim 1, characterized in that a compound is used as the active ingredient is used, which by the action of 2-formyl-4-chlorophenol or one of its salts to an ester of the general formula X - CH - CO - Z CH ₃ or one of its salts, in which X is a reactive organic or inorganic ester radical represents and Z has the above meaning has been produced. 409 599/305 6.64 © Bundesdruckerei Berlin