DE2732141A1 - PROPYL-3-TERT.-BUTYLPHENOXYACETATE, METHOD FOR THE PRODUCTION THEREOF AND ITS USE AS A PLANT GROWTH REGULATOR - Google Patents

Description

UH. INfJ. K. WirHSTIIOHH I> K. K. ν. PKOlI MAN I) H. IN". 1). HKII It KNS DJPL. JN (i. H. ΚOKTZ PATENT LAWYERS

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τκι.κκοΝ (OMO) UOXUOJ

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TKI.KORAMMK ι PMOTKCTPATKItT ΜϋΚΟΠΒΜ

1A-49 657

Patents me 1 d u η

Applicant: MAY & BAKER LIMITED

Dagenham, Essex, England

Title: Propyl 3-tert-butylphenoxyacetate, Procedure

for its manufacture and its use as a plant growth regulator

709885/0718

UR. ING. F. WUKSTHOFF

DH. Κ. ». PKOLIM ANN UH. ING. U. BKURKNS UIPLJNU. U. CiOKTZ PAT EN TAN Wl LTE

HOOO MUNCHKNOO

SiIlWKIOKUNTItASSK 3 τκι.κΓοκ «081») TKI.KI S 2 * OTO TKLKOHAMMK:

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Applicant: May & Baker. · ..

description

The invention relates to a new agriculturally useful ester, to processes for its preparation and its use as an agent for regulating plant growth and agents that use this ester as an active ingredient contain.

As a result of research and experiment, it was found that Propyl-3-tert-butylphenoxyacetate, that of the formula

OCH ₂ COO (CH ₂ ) ₂ CH,

corresponds to valuable plant growth regulating properties unfolds when applied to actively growing or dormant plant tissue. This connection can therefore with Advantageously, they can be used to influence the growth of economically valuable plants, for example for improvement the quantity or quality of the expected harvest or the harvest yield and repairs the farmer in a simple manner exercise greater control over the growth process or facilitates handling, especially mechanical handling of the crops, for example when harvesting. Depending on the type of application and the growth stage of the plant tissue, which is treated with it causes the application of propyl-3-tert.butylphenoxyacetate stimulation and enhancement of plant growth or inhibition of plant growth.

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For example, the use of the compound of the formula I has the following consequences:

a) Increase in the yield of fruit-bearing trees, especially apple, pear, cherry, plum, lemon and oil palm trees,

(i) by improving the tree form by the "feathering" or "feathering ¹¹ (feathering) is animated by 1 year old GewSchsen from the nursery or incited by the tip growth of the strain is controlled without killing the apical meristem and a strong lateral Branching is initiated above the point of application (usually to the top 20 to 50 cm of the tree), with a desired wide bifurcation angle between the lateral branches and the trunk

of the first tree that has not yet borne fruit and / or secondary lateral branches on 2 or 3 year old plants after transplanting in the orchard, produced by application during the annual period of vigorous growth will;

(ii) for fruit trees such as apple, pear, cherry and plum trees, by reducing the vegetative growth period before a noticeable crop of fruit is produced after transplanting from the nursery to the field (orchard); In general, in the case of apple trees, in the case of trees, the treatment according to (i) the growth period has been reduced from 2 years to 1 year.

For this purpose, i.e. for purposes a) (i) and (ii), propyl 3-tert-butylphenoxyacetate is expediently in the form used by sprays and similar agents that contain 750 to 1500ppm of the active ingredient.

b) Improvement of the shape of ornamental, i.e. decorative plants both from plants grown in containers (pots), such as Cornus sp (dogwood, hornbeam) and from in the Nursery-grown ornamental plants such as Acer sp (for example

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Maple); this supports vigorous bushy growth and, in the case of trees, fletching ^11. For this purpose, propyl 3-tert.butylphenoxyacetate is advantageously used in the form of sprays and similar agents which contain 750 to 4000 ppm of this compound.

c) Improvement of the fruit quality, especially with apples and Grapes by the full bloom, young fruit sets and intermediate stages are thinned out by using this By means of these growth stages. For this purpose it is expedient Propyl-3-tert-butylphenoxyacetate applied in the form of sprays and similar application forms, the 250 contain up to 1500 ppm of the active ingredient.

d) To improve the yield of widely grown crops such as cotton, soybeans, field beans, dwarf beans, Peanuts, rapeseed and sunflowers, especially when used in the flowering stage, for example on a cotton plantation. For this purpose, propyl 3-tert-butylphenoxyacetate is expediently used in amounts of 0.56 to 2.24 kg of active ingredient per ha applied.

or thinning out

e) Chemical cleaning / of young plantings, for example tea plantings by inhibiting side growth · To for this purpose propyl-3-tert.butylphenoxyacefet is used in the form applied by sprays or similar forms containing 750 to 3000 ppm active ingredient.

f) Defoliation of plants from sanctuaries or tree nurseries

(i) by applying the agent at the end of the growing season, whereby transplanting and controlling plant diseases is facilitated, for example in the case of of roses and Quercus rubra (red oak) and fruit trees such as apple trees and hedges as well

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(ii) by application before flowering, for example with jasmine, in order to subsequently increase the yield of flowers per bush or reinforce.

For this purpose, i.e. for f) (i) and (ii) propyl-3-tert-butylphenoxyacetate is used expediently applied in the form of sprays or similar preparations containing 1000 to 10,000 ppm of active ingredient contain"

g) Increasing the number and yield of potato tubers. Propyl-3-tert.butylphenoxyacebt is expediently used for this purpose applied in the form of sprays and similar agents containing 1000 to 3000 ppm of active ingredient.

h) improving the yield and reducing the loss in harvesting Brussels sprouts by the application of the agent during the period when the buds or shoots form as a substitute for the hand ^entfer 85fcale outermost tip of the plant. For this purpose propyl-3-tert.-

butylphenoxyacetate conveniently applied in the form of sprays and similar preparations containing 4000 to 6000 ppm of active ingredient contain.

i) Prevention or suppression of unwanted side growth, for example side shoots or side shoots of tomato plants. Propyl 3-tert.butylphenoxyacetate is suitable for this purpose applied in the form of sprays and similar agents containing 3000 ppm of the active ingredient.

j) Improving the yield of monocotyledonous crops like wheat, barley and rice by increasing the number of tillers and / or reducing the number of pigeons For this purpose propyl-3-tert.butylphenoxyacetate is expediently used applied in the form of sprays and similar agents containing 200 to 2000 ppm of active ingredient.

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rr, iz ζ pointed. Attempt 1

z rr

An _S pray _fl U _Ssig Keit containing 050 ppm ph.noxy.o * t, the following by diluting the liquid agent described Io 5 was obtained with water, was sprayed in the early summer to 70 cm high fruit trees, until the liquid from the Leaves dripped down. The effect on the side branches of the trees compared to untreated trees was assessed in early spring of the following year. The results, obtained as the mean value for 7 trees per treatment, are listed in Table 1 below:

Table 1

Tree variety number of side branches with at least

5 cm length

treated untreated

3.7 6.2 6.7 3.3

This experiment shows the increase in side branches caused by the application of propyl-3-tert-butylphenoxyacetate to apple and pear trees is evoked.

Attempt. 2

Pear Cornice 1.1 Apple Bramley 1.3 Apple Red Miller 2.8 Apple Spartan 1.0

A spray liquid containing 900 ppm propyl 3-tert-butylphenoxyacetate was prepared by diluting the liquid agent described in Example 5 below with water and

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on nursery apple trees (variety Bramley) in early summer sprayed on until the agent dripped off the leaves. The treatment was repeated 2 years later, also in early summer and in the year following the second treatment determines the mean number of flower clusters per tree in spring and compared with the corresponding number in fruit trees that had been cleaned by hand in the usual way. the The results are summarized in Table 2 below:

Table 2

average number of flower clusters per tree

valuation

spiny, spur and axillary terminal

Control 6.14 2.42

according to the invention ^ ₂ ^, " ₂ "

treated

This experiment shows the increase in the number and lateral branches and the improvement in the shape of the trees, which is expressed in the increase in the number of flower clusters that through the use of propyl-3-tert.butylphenoxyacetate 2 and 3 year old apple trees versus untreated, hand-cleared trees.

Attempt 3

The liquid agent described in Example 5 below was diluted with water and added in a dose of 0.56 kg, 1.12 kg and 2.24 kg propyl-3-tert-butylphenoxyacetate per hectare a cotton plantation sprayed ^ 2 or 4 weeks after the full bloom. The increase in cotton yield per hectare in comparison with untreated plantings was assessed at harvest; the results are summarized in Table 3 below.

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T a b le 1 e 3

Active ingredient dose

kg / ha

Time of treatment (weeks after full bloom)

2 weeks 4 weeks cotton yield Cotton yield kg / ha kg / ha

0.5 pounds 999 1.12 1156 2.24 958 not treated delt (con 804 trolls)

1086 1064 1014

804

This experiment shows the increase in the yield of cotton with Propyl 3-tert-butylphenoxyacetate was treated.

The compound of the formula I according to the invention can be prepared by converting a compound of the general formula:

OCH ₉ COX

* · II

(in which X is a halogen atom, preferably a chlorine atom, a hydroxyl group or another alkoxy group with 1 to 6 carbon atoms than the propoxy group) with propanol.

The implementation of the compound of formula II in which X is a hydroxy group means that propanol can be carried out in the presence of an acidic catalyst, e.g. hydrogen chloride gas, sulfuric acid or p-toluenesulfonic acid, optionally in the presence of an inert organic Solvent, e.g., toluene, or an excess of propanol can serve as the solvent under suitable anhydrous conditions at an elevated temperature, for example between 80 and 120 ° C, preferably at the reflux temperature of the reaction mixture.

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The reaction of a compound of the formula II in which X * is a feirr lfajogen atom with propanol can, if necessary, in the presence of an acid-binding agent, e.g. triethylamine or pyridine, and if necessary in the presence of an inert organic solvent, e.g. carbon tetrachloride, chloroform or toluene , be carried out at room temperature or elevated temperature, for example between room temperature and 12O ° C un
mix.

120 C and preferably at the reflux temperature of the reaction

The transesterification of a compound of the formula II in which X is an alkoxy group other than the propoxy group with propanol can be carried out in the presence of an acidic catalyst, for example hydrogen chloride gas, sulfuric acid or p-toluenesulfonic acid, if appropriate in the presence an inert organic solvent or an excess of propanol as solvent under substantially anhydrous conditions at an elevated temperature, for example between 60 ° and 12O ⁰ C
Reaction mixture.

see 60 and 120 C and preferably at the reflux temperature of the

According to the invention, the compound of the formula I can also be prepared by reacting a compound of the general formula

III

(CH ₃ ) ₃ C '

(in which M is an alkali atom, e.g. sodium or potassium) with a Compound of the general formula:

YCH ₂ COOR IV

(in which Y is a halogen, e.g. a chlorine atom and R is an alkyl group

man

with 1 to 6 carbon atoms) and then if the Reaction partner of the general formula IV is a compound in which R is not the propyl group, the transesterification described above performs.

709885/0718

INSPECTED

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en * FcJfmeinτ *

* 3

Implementation between the links of the general! III and IV can be added in the presence of an anhydrous inert organic solvent, e.g. dimethylformamide or propanol at a temperature between 0 and 100 C.

The compound of formula II in which X is a hydroxy group can be prepared by applying or adapting known ones Process for the production of phenoxy acetic acids.

The compounds of formula II in which X is a halogen atom can be prepared by applying or adapting known ones Process for the preparation of acid halides from carboxylic acids, i.e. the compound of formula II in which X is a hydroxyl group is.

The compounds of the formula II in which X is a halogen atom can optionally be used without further purification.

The compounds of formula II in which X is a different alkoxy group than the propoxy group can be prepared by Use or adaptation of known processes for the preparation of carboxylic acid esters, e.g. the processes for preparation described above the compound of formula I.

The compounds of formula III can be prepared from 3-tert-butylphenol (a known compound) can be prepared by applying or adapting known methods for the preparation of alkali salts of phenols.

The compounds of Formula IV can be prepared by using or adapting known methods for the preparation of Monohaloacetic acid esters.

The term "known methods" as used here is to be understood as meaning methods which have been used or are in have been described in the chemical literature.

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INSPECTED

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The invention also relates to a method of regulating plant growth, such as that described above, which is used therein consists that one is on actively growing or dormant plant tissue an effective amount of the compound of formula I applies. For this purpose, the compound can be used alone or in the form of Agents for regulating plant growth (i.e. together with one or more compatible diluents or carriers, suitable for such agents) are used, e.g. explained in more detail later. Suitable methods of application are, for example: Application to 1-year-old nursery fruit trees by direct spraying e.g. with ultra-small volume and foams and on growing plants by spraying the leaves and stems.

Particularly important methods include a method for stimulating the "fletching" of 1 year old nursery fruit trees, especially apple and pear trees, by applying the compound of formula I, preferably in the form of an agent, for example a spray containing between 0.075 % (750 ppm ) and 0.15 % (1500 ppm) (weight) of the

the Trxebe binding of formula I to the tip / 20 cm wxs 50 cm from the vegetation score - until it "runs off" in the case of sprays, except when used of an ultra-small volume, e.g. 50 liters of spray liquid or less per hectare as well

a method of forming secondary side branches in 2 and 3 year old fruit trees after transplanting in orchards by applying the compound of formula I preferably in the form of an agent such as a spray containing between

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0.125 % (1250 ppm) and 0.15 % (1500 ppm) (weight) of the compound of the formula I to run-off in the case of sprays.

The invention also relates to liquid compositions that act as plant growth regulators can be used containing as active ingredient the compound of formula I, together with one or several diluents or additives that are compatible with the compound of formula I and used in such agents can be.

Liquid agents according to the invention can take the form of solutions, Possess suspensions and emulsions of the compound I, which preferably contain wetting agents, dispersants or emulsifiers. These emulsions, suspensions and solutions can be prepared using aqueous organic or aqueous-organic diluents, e.g. acetophenone, cyclohexanone, isophorone, Toluene, xylene, dimethylformamide and mineral, animal and vegetable oils (and mixtures of these solvents), the wetting agents, Dispersants and emulsifiers, which can be ionic or non-ionic, as well as mixtures thereof, e.g. as described later.

If necessary, the emulsions or solutions containing the compound of Formula I contain, can be used in the form of self-emulsifying or self-dissolving concentrates, containing the effective Substance dissolved in the emulsifying or wetting agents or in solvents containing emulsifying or wetting agents with the active ingredient are compatible, means for direct application being created by simply adding water to such concentrates.

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The wetting agents, dispersants and emulsifiers used in the agents according to the invention can be present, can be ionic or non-ionic, for example SuIf hear icimleate, quaternary ammonium derivatives or products based on condensates of ethylene oxide with nonyl and / or octylphenol or Carboxylic acid esters of anhydrosorbitol which have been made soluble by esterification of the free hydroxyl groups by condensation with ethylene oxide or mixtures of such agents.

The invention also relates to agents capable of foaming to build.

Agents according to the invention can also contain auxiliaries. the Agents can be mixtures of the auxiliaries and the compound of the Formula I in the form of preparations or mixtures. Examples of such auxiliary compounds or additives include Insecticides such as organic phosphoric esters, e.g. parathion, i.e. (^ O-diethyl-O- ^ nitrophenyl-phosphorothionate, malathion, i.e. S-11,2-di (ethoxycarbonyl) ethyl 0,0-dimethyl-phosphorothiolothionate, vamidothione, ie OjO-dimethyl-Sp-il-methylcarbamoylethylthio) ethyl / phosphorothiolate, diazinon, ie 0,0-diethyl-0- | 2-isopropyl -6-methylpyrimidin-4-ylJ phosphorothionate, monocrotophos, ie 0,0-dimethyl-cis-1-methyl-2- (N-methylcarbamoyl) vinyl phosphate, dimethoate, i.e. O, O-dimethyl-S- (N-methylcarbamoylmethyl) phosporthiolothionate, phosalone, i.e. S- (6-chloro-2-oxobcn- zoxazolin-3-yl) methyl-0,0-diethyl-phosphorothiolothionate, bromophosethyl, ie 0- (4-bromo-2,5-dichlorophenyl) -0,0-diethyl phosphorothionate, carbamates, eg carbaryl, ie 1-naphthyl -N-methyl-

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carbamate, formetanate, i.e. 3-dimethylaminomethyleneimino-phenyl-N-methylcarbamate, pyrethrins (natural and synthetic), e.g. bioallethrin, chlorinated hydrocarbons, e.g. DDT, i.e. 1,1,1-trichloro-2,2-l> is (p- chlorphenyl) ethane, as well as mixtures with the ο, ρ ¹ -isomer, BHC, i.e. mixture of isomers of I, 2,3>4i5> 6-hexachlorocyclohexane, toxaphene, i.e. camphechlor (an isomeric mixture of chlorinated camphenes containing 67-69 % Chlorine), dichlorobenzene, acaricides, e.g. quinomethionate, ie 6-methyl-2,3-quinoxaline diylcyclic- "SjS-dithiocarbonate, dicofol, ie 2,2,2-trichloro-l, 1-bis (p-chlorophenyl) ethanol, and tetradifon, ie 2,4,4 ', 5-tetrachlorodiphenyl sulfone, non-insecticidal compounds such as the synergistic methylenedioxyphenol derivatives, for example piperonyl butoxide, ie 5- [2- (2-butoxyethoxy) ethoxymethylJ-6-p. ropyl-1,3-benzodiaxoJ., Sesamex, ie 2- (3> 4-methylenedioxyphenoxy) -3,6,9-trioxaundecane, 0,0-dimethyl-O-phenyl-phosphorothioate; fungicidal compounds, for example copper sulfate, dinocap, ie a mixture of 2.6 Dinitro-4-octylphenyl crotonates and 2,4-dinitro-6-octylphenyl crotonates ("octyl" denotes the isomeric radicals 1-methylheptyl, 1-ethylhexyl and 1-propylpentyl), chloroxylenol, ie 4-chloro-3,5-xylenol, thiophanate methyl , ie l, 2-bis (3-methoxycarbonyl-2-thioureido) benzene _i dichlorophene, ie bis (5-chloro-2-hydroxyphenyl) methane, and thiram, ie tetramethylthiuram disulfidj preparations of Bacillus thuringiensis (toxins and organisms) and Insect viruses.

Many additives are known. The only requirement is that they should be compatible with the compound of Formula I as well with other components contained in the means.

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The agents according to the invention generally contain 0.05 to 90 % (w / v) of the compound I and are used in such an amount that they have the desired effect as by the user or another person skilled in the art, depending on the plants to be treated is to be assessed.

The following Examples 1 to 4 illustrate the preparation of the compound according to the invention.

example 1

10.4 g of 3-tert-i-butylphenoxy-acetic acid were dissolved in 80 ml of propanol Heated under reflux for 2 hours, a stream of hydrogen chloride being passed through. The excess propanol was distilled off and the residue dissolved in 75 ml of diethyl ether. The ethereal solution was successively with saturated aqueous sodium bicarbonate solution washed and water, dried over sodium sulfate, filtered and evaporated to dryness. The oily residue was distilled. 8.5 g of propyl-3-tert-butylphenoxy were obtained acetate, K.p. 179-180 ° C / 18 mm Hg, as a colorless oil.

Example 2

920 g of 3-tert-butylphenoxyacetic acid were added with 920 ml for 2 hours Thionyl chloride heated under reflux. The excess thionyl chloride was evaporated. Last traces of thionyl chloride were found removed by heating in the presence of 2 × 500 ml of toluene. That Crude 3-tert-butylphenoxyacetyl chloride was slowly added to 6.5 liters of refluxing propanol and after the addition the solution was refluxed for 2 hours.

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The excess propanol was distilled off in vacuo. The residue was distilled. 1068 g of propyl-3-tert-butyl were obtained phenoxyacetate, K.p. 170 C / l2 mm Hg, as an almost colorless oil.

Example 3

12.1 g propyl chloroacetate in 10 ml dry dimethylformamide became a solution of sodium 3-tert.-butylphenoxide with stirring (prepared from 10 g of 3-tert-butylphenol and 1.64 g of sodium hydride) in 50 ml of dry dimethylformamide at 10 ° 15 C given. The mixture was stirred at room temperature for 2 hours and evaporated to dryness. The residue was in a mixture of 100 ml of chloroform and 100 ml of water. The organic layer was separated over magnesium sulfate dried, evaporated and distilled. 10.3 g of propyl 3-tert-ethylphenoxyacetate, K.p. 176-178 C / 20 mm Hg, as a colorless oil.

Example 4

27.9 g of methyl 3-tert-btitylphenoxyacetate, (] tp. 6l-162 ° C / 20 mm Hg) were prepared similarly as described above in Example 2, but using methanol instead of propanol,) dissolved in 45 ml of propanol. The solution was heated to reflux for 1.5 hours while flowing in a stream of hydrogen chloride was passed through. The excess propanol was evaporated and the residue was dissolved in 75 ml of diethyl ether. The ethereal solution was successively with saturated aqueous sodium bicanjmat solution and water, dried over sodium sulfate, fil-

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trated and evaporated to dryness. The oily residue was

distilled. 23 g of propyl-i-tert-butylphenoxyacöt'ät, K.p. 173-175 ° C / 15 mm Hg, as a colorless oil.

The following examples illustrate compositions according to the invention Middle.

Example 5

A liquid agent in the form of a concentrate was prepared by mixing

Propyl 3-tert-butylphenoxyacetate 90 % w / v.

Duoteric MBl 5% "

Duoteric MB2 5 % »

Example 6

A liquid agent in the form of a concentrate was prepared by mixing

Propyl 3-tert-butylphenoxyacetate 60 % w / v

Arquad 2C-75 5 % "

Ethofat 142/20 S% ⁿ

Aromasol H. to 100 % ( vol.)

Example 7

A liquid agent in the form of a concentrate was prepared

by mixing

Propyl 3-tert-butylphenoxyacetate 20 % w / v

Duoteric MBl 5% ⁿ

Duoteric MB2 5 % »

Cyclohexanone - 3 volumes)

) to 100 % (vol.)
Xylene - 1 volume) " ¹ 7-

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Liquid agents of the type specified in Examples 5-7 can be diluted with water to form emulsions containing 0.05 to 8.0 % (w / v) propyl-3-tert.-butylphenoxyacetate (1-4 kg in 50%) -2,000 1) as sprays. For example can

a) the liquid agent according to Example 5 with water in an amount diluted by 1 ml of the agent to 1 l of water and on the tips of the shoots to 20 - 30 cm from the vegetation points of 1 year old tree nursery fruit trees, e.g. apple and pear trees will. This treatment results in a strong lateral branching with a desirably wide bifurcation angle between the lateral branches and the trunk;

b) the liquid agent of Example 6 is diluted with water to a concentration of 10,000 ppm (6,000 ppm propyl-3-tert-butylphenoxyacetate) and sprayed on Brussels sprouts when the first 5 or 6 lower buds are 1 cm in diameter own. This treatment serves as a substitute for removing the topmost tip of the plant by hand and lessening it the waste from harvesting the Brussels sprouts;

c) the liquid concentrate according to Example 7 is diluted with water to a concentration of 1250 ppm (250 ppm propyl-3-tert.-butylphenoxyacetate) and sprayed on apple trees with young fruits. This treatment reduces the number of Fruits and increases the size and quality of the remaining fruits.

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Example 8

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Propyl-3-tert-butylphenoxyacetate can be used undiluted in an amount of 1-2 kg / ha are sprayed using appropriate spray devices for ultra-small volumes.

To improve the spray cover, 1-5 l / ha of a non-phytotooci can see Sprays with propyl-3-tert-butylphenoxyacetate before mixed with the application.

Propyl-3-tert-butylphenoxyacetate can be sprayed on cotton in an amount of 1 kg / ha 2 weeks after full bloom, to increase the cotton yield.

Example 9

A liquid agent in the form of a concentrate was prepared by mixing

Propyl 3-tert-butylphenoxyacetate 10 % w / v

Ethylan KEO 10 % »

Dimethylformamide 'to 100 % vol.

This agent can be diluted with water to a clear solution containing 0.05 % (500 ppm) to 4.0 % (40,000 ppm) w / v propyl 3-tert-butylphenoxyacetate for spraying.

A spray liquid obtained in this way containing 40,000 ppm of the agent (4,000 ppm propyl-3-tert-butylphenoxyacetate) can be used Sunflower plants sprayed approximately 40 days after sowing will. This treatment increases the seed yield and the mean seed weight.

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Example 10 %?O

Agents of the type indicated in Examples 5, 6, 7 and 9 can be added to an aqueous solution containing 1% Perlankrol ESD-60 to achieve a concentration of 0.05 to 1.0 % (w / v) Propyl-3-tert .- "b'utylphenoxyacetate to obtain the agent in the form of a foam with the help of special foam-producing

of the hydraulic nozzles.

The trade names used in the description have the following meaning:

Ethylan KEO (solubilizer): Nonyl-phenol-ethylene oxide condensate (10 moles of ethylene oxide);

Duoterics MBl and MB2 (emulsifiers): Mixture of anionic and non-ionic emulsifiers containing calcium alkyl aryl sulfonates and alkyl phenol ethylene oxide condensates; Perlankrol ESD-60 (foaming agent): sodium salt of a synthetic primary alcohol-ether-sulfate;

Ethofat 142/20 (emulsifier): fatty acid-ethylene oxide condensate.

Arquad 2C-75 (emulsifier): Di-coco-dimethyl-ammonium-chloride ("coco" refers to alkyl groups derived from coconut oil);

Aromasol H is a hydrocarbon oil containing 95 aromatics (K.p. 168 ° - 200 ° C).

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ORIGINAL INSPECTED

Claims (10)

Claims c "h e f 1. j propyl 3-tert-butylphenoxyacetate. 2. Process for the preparation of the compound according to claim 1, characterized in that one A) a compound of the general formula: (CH,), C. OCH ₂ COX in which X represents a halogen atom, a hydroxyl group or another Means alkoxy group having 1 to 6 carbon atoms as the propoxy group, reacted with propanol or B) a compound of the general formula: in which M is an alkali atom, reacts with a compound of the general formula: YCH ₂ COOR in which Y is a halogen atom and R is an alkyl group with 1 to 6 carbon atoms and then, if in the compound IV R is not a propyl group, the resulting alkyl 3-tert.-butylphenoxyacetate according to known methods - 709885/0716 ORIGINAL INSPECTED drive transesterified. 3. The method according to claim 2, characterized in that the reaction A when X is a hydroxyl group or an alkoxy group other than the propoxy group, the reaction in the presence of an acidic catalyst and optionally in the presence of an inert organic solvent or an excess of propanol as a solvent under im performs essential anhydrous conditions at elevated temperature. 4. The method according to claim 2, characterized in that the reaction A when X is a halogen atom is, optionally in the presence of an inert organic solvent at room temperature or elevated temperature performs. 5. The method according to claim 2, characterized in that reaction B is carried out in the presence of an anhydrous inert organic solvent at a temperature between 0 and 100 ^° C. 6. Liquid funds for use as plant growth regulators, characterized in that it contains the compound according to claim 1, optionally as active ingredient together with one or more liquid diluents or additives. 7. Composition according to claim 6, characterized in that it contains at least one wetting agent, dispersing agent or contain emulsifying agents. -3- 709885/0718 _3_ 27 32 H1 8. Composition according to claim 6 or 7, characterized in that the diluent is water. 9. Composition according to claim 6 to 8, characterized in that it Q05 to 90% (wt./lfol.) Contain active ingredient. 10. Use of the compound according to Claimi or the Agent according to Claims 6 to 9 for regulating plant growth. 709885/0716