DES0033320MA - - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

Registration date: May 5, 1953. Advertised on February 9, 1956

GERMAN PATENT OFFICE

. The invention relates to new and improved compositions for treating growing Plants to influence the normal course of life of these plants in a certain way. Namely it refers to phytotoxic mixtures containing at least one of the 3,6-endoxyhydroorthophthalic acids as effective, d. H. Contain component acting on the plants.

Phytotoxic mixtures with at least one of the acids mentioned, in particular the 3,6-endoxyi, 2,3,6-tetrahydro-o-phthalic acid and / or the 3, 6-endoxyhexahydro-o-phthalic acid, be it as such or in the form of equivalent derivatives, and in particular the exocis isomers of these acids, are for the mentioned purpose highly effective. According to the invention, mixtures are used which have the above contain active ingredients mixed with simple, easily accessible ingredients which increases or strengthens the effect of the endoxyhydroorthophthalic acids which affect the plants will.

Patent 898,308 relates to plant treatment agents with 3, 6-endoxyhydro-o-phthalic acids (namely 3, 6-endoxyhexahydro-o-phthalic acid and the 3, 6-endoxy-i, 2, 3, 6-tetrahydro-o-phthalic acid) and their derivatives as an active substance. These substances produce certain desirable properties in plants Effects such as total or partial elimination of leaves and germs, reduction of the flower base, complete destruction of the plant,

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additional root formation or delay in fruit shedding. The type of action on the plant depends on the concentration of the agents used and on the type and state of growth of those treated _; Plant down.

The substances mentioned, which act on the plants, can either as such or in the form of their chemically equivalent derivatives are used, e.g. B. their anhydrides and / or a salt in which,

ίο just like in the acids themselves, the corresponding ones Anions of the ortho compounds are included, these anion compounds either acidic or have a neutral character and can be chemically bound to equivalent amounts of cations,

z. B. to one or more metal and / or radical cations, such as sodium, potassium, calcium, strontium, magnesium, aluminum, iron, cobalt, nickel, Cadmium, mercury, copper ions, ammonium, mono-, di- or trialkylammonium, mono-, di- or trialkanolammonium and mixed alkylalkanolammonium radicals.

Here, the acid is the active ingredient, regardless of whether it is as such or in the form of a salt or anhydride or in any other equivalent form. These changes to the carboxyl groups are only those of the form, but not those of the basic substance.

In describing the invention, for the sake of simplicity, with reference to the 3, 6-endoxyhexahydro-o-phthalic acid and the 3, 6-endoxyi, 2, 3, 6-tetrahydro-o-phthalic acid (as such or as their chemically equivalent Derivatives) is described in more detail with regard to their activity as active ingredients in the new plant treatment mixtures, it should first be emphasized that most of these acids are fairly soluble in water. The other forms used with the same anions are also water-soluble, some of them even very strongly, while with others the solubility in water is not so pronounced. Of course, preference will be given to those compounds whose solubility in water is at least 0.1 percent by weight and, if possible, even more than 1 percent by weight.

The water solubility is therefore desirable so that anions (acidic or neutral or both) are formed, if the acids as such or in a chemically equivalent form are dissolved in water.

Acid anions can theoretically with reference to the acidic 3,6-endoxyhexahydro-o-phthalate anion explain what a monovalent anion with the following structural formula is to be understood:

CH ₉

CH ₉

.CH.

CH

CH-C-O

CH-C-OX

where X is a cation, according to current Conception of hydrogen. Neutral anions can theoretically with reference to the neutral

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3,6- Endoxyhexahydro - ο - phthalate - anion explained ^: including a divalent anion of the structural formula

CH ₉

CH ₉

CH.

CH-

CH-C —0 -

CH-C —O -

CH.

R O

CH

CH-C-O
CH-C-OY

is to be understood. Analogous anions are formed when the tetrahydroacid or its chemically equivalent Forms to be dissolved in water.

So can the mentioned; active ingredients are defined as compounds which, in the presence of Water give anions of the following structure:

where Y is a free valence or a cation and R is a vinylene or ethylene radical.

Although the invention is not bound by any particular theory explaining the process of the reaction should be, through which the particularly beneficial effects on plants are caused, extensive research has made it very likely that those mentioned Effects due to the presence of anions (acidic and / or neutral) of the specified type in aqueous medium.

The anions mentioned are available because the acids as such or in the form of equivalent Derivatives are water soluble and ionizable. Therefore, such a connection dissolves when it is disconnected from the Vascular system of a plant is absorbed in the aqueous plant sap and brings the anions to act. The acids as such or their equivalent derivatives are thus considered to be very useful Consider means to deliver the desired anions in absorbable form to the plant.

It follows from this that the acids as such and their salts or anhydrides can be used equally well.

It was found that the for. Achieving a The quantities of these compounds required for certain effects on the plants are significantly reduced can be, or that the action of a certain amount of the active ingredient on the Plants can be increased noticeably if one or more saturated, Pepper-chain mono- or dioxy-mono-, -di- or -tricarboxylic acids with carbon chains of 2 to 6 carbon atoms and their ammonium or substituted ones Adds ammonium salts, which salts can be either neutral or acidic. Of the substituted Ammonium salts are especially the alkylammo-

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nium, alkanolammonium and the mixed alkylalkanolammonium salts useful.

As oxycarboxylic acids of the type just mentioned, glycolic acid, lactic acid, hydracrylic acid, the various Oxybutteric and oxyaleric acids, ε-oxycaproic acid, α, y-dioxybutyric acid, glyceric acid, Tartronic, malic and tartaric acid, citramalic acid and citric acid should be mentioned. Examples of Salts of such oxy acids are ammonium salts, including the neutral ammonium salts in the case of dicarboxylic acids also the acidic ammonium salts and the primary and secondary alkylammonium salts ι to 4 carbon atoms in each alkyl radical, mono-, di- and trialkanolammonium salts having 2 to 3 carbon atoms in each alkanol radical and mixed alkylalkanolammonium salts. The substituted ammonium salts include both neutral and acidic salts, quite analogously to the ammonium salts described above. In the cases of salts with more than one ammonium and / or substituted ammonium radical (i.e., cations) these cations can be the same or different from one another.

The preparation of the salts according to the invention can be carried out in any manner known to the person skilled in the art take place, e.g. B. by neutralizing a certain acid with the calculated amount of the desired Base or the base mixture. In general, water is an excellent solvent for penetration conduct such neutralizations, although other solvents can sometimes be advantageous.

The 3, 6-endoxyhydro-o-phthalic acids can also be used as such or in the form of their chemically equivalent Prepare derivatives in any manner known to those skilled in the art.

The amounts of additives or enhancers that have to be added to the Endoxo compounds can vary within a very wide range, and even a very small addition of the enhancer. causes a considerable synergistic increase in effectiveness. In general, quantitative ratios of enhancer to active constituent between 1:10 and 50: 1, in particular between 1: 1 and 20: 1, are expedient for practical purposes.
. The enhancer and the active ingredient can be mixed purely mechanically with one another in any desired manner, in particular when the enhancer is in solid form or as a solution in a common solvent such as water. In the latter case, the solution can be placed on the market as such or in a dried form, which can be achieved by spraying or drum drying, especially if the enhancer is usually solid. In any case, it is preferable to use a solid mixture, finely divided and in such a dry state that it can be poured easily.

The mixtures can be added to the plants or seeds in any desired manner, so in solid form, for example by dusting, or as a liquid, e.g. B. by spraying.

Further mixtures according to the invention can also be used. common in atomization technology Additives are incorporated, such as any known liquid or solid carriers, preferably those solid support with a large particle surface, such as clay, fuller's earth, pyrophyllite, talc,. Bentonite, kieselguhr, Diatomaceous earth, etc. Any finely divided commercially available clay can be used, especially those commonly used as carriers for insecticides. The commercially available clays are mostly identified by certain brand names (which indicate the origin and processing), of which Homer clay, Celite and Tripoli are mentioned as typical. .

Other non-clayey additives for incorporation into the mixtures mentioned are e.g. B. sulfur, volcanic ashes, calcium carbonate, quicklime, lignin-containing waste materials, wood pulp, flours, e.g. B. made of wood, walnut shells, wheat, soybeans, potatoes, cottonseed, etc.

Known methods can be used to prepare the mixtures. So can the active ingredients ground to a fine powder and stirred or shaken with the amplifier, namely if this is also firm; to a certain extent, however, some of these components can also be used be mixed in liquid form with the remaining solid, pourable mixtures, or the Enhancer and the active ingredient can be ground together right away; also one can active ingredient in liquid form (e.g. in the form of its solutions, dispersions, emulsions and suspensions) Mix with the amplifier in a fine distribution and in proportions such that a good pourability of the product is guaranteed, or you proceed the other way around. One can but also remove an excess of liquid, e.g. B. by evaporation, about under reduced pressure. The same is true of mixtures of the active ingredients and enhancers with any finely divided solid carriers and / or other additives.

When preparing solid mixtures, it is important that the mixture be in a finely divided form. The dust containing the active agent should be so fine that almost no residue remains on a sieve with a clear mesh size of 0.25 mm, if possible not even on a sieve with a clear mesh size of 0.07 mm. Excellent results were obtained when the pulverulent mixture contained predominantly particles on the order of 15 to 45 / t. Even finer dust, e.g. B. with particle sizes of about 5 μ and less, have very good hiding power, but tend to be blown away when applied and are also more expensive to manufacture.

For spraying, the mixture is dissolved or dispersed in a liquid carrier such as water or in another usable liquid.

So you can get the mixtures of the active ingredients in the form of solutions, suspensions, dispersions or use emulsions in aqueous or non-aqueous media. ,

Emulsions or dispersions of the mixtures in the liquid carriers can be obtained by stirring the Mixtures with the carrier can be obtained. Preferential

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wisely, however, one stirs in the presence of an emuig or dispersant (a surface active agent) to help form the emulsion or dispersion to facilitate. Emulsifiers and dispersants are well known in the art; belong to them e.g. fatty alcohol sulfates, such as sodium lauryl sulfate, aliphatic and aromatic sulfonates, such as sulfonated castor oil or the various alkaryl sulfonates, such as the sodium salt of the monosulfonated

ίο nonylnaphthalene or tertiary dodecylbenzyl, and non-ionic types of emulsifying and dispersing agents, such as the high molecular weight alkyl polyglycol ethers or the. analogous thioethers, such as the decyl, dodecyl and tetradecyl polyglycol ethers and thioethers with 25 to 75 carbon atoms.

Also the use of aids such as wetting agents and / or humectants (water-retaining Medium), is suitable for the solutions of the mixtures according to the invention, namely for the aqueous solutions. Any known wetting and humidifying agents can be used for this purpose, like the wetting agents described in more detail above. Examples of humectants are glycerin, ethylene glycol, Di- and polyethylene glycols and water soluble Sugar and mixtures containing sugar, such as glucose, fructose, calactose, mannose, arabinose, Xylose, sucrose ,. Maltose, lactose. Raffinose, trehalose, or dextrins, such as white or yellow Dextrin, British gum etc, honey, molasses, maple syrup and sugar, and corn syrup such as corn syrup etc.

As an aid one can apply any desired amount of wetting agent, up to 250 or more so ° / ₀ of the active ingredient. For wetting, the amount of additive used can be measured so that the desired wetting properties are given to the finished solution to be sprayed, so z. B. 0.05 percent by weight of this solution. The use of significantly higher amounts is no longer based on their network properties, although these are present. but is a function of the physiological behavior of the wetting agent after it has been sprayed onto the plant.

Although the mixtures of the active ingredients with the enhancers affect the growing plants in Concentrated form can be applied, it is usually desirable, liquid or solid preparations apply in which the active ingredient is less than 30% by weight of the total amount matters, e.g. B. less than 10 and even only o, i ° / o In practice, the procedure, if it is used for defoliation purposes, depends on the one used Amount of the. Type of plants to be treated and their state of maturity. In any case is the amount of the active ingredient necessary for the achievement of a certain effect in the same Plant species required is much lower than when no intensifier is present.

As a general rule of application it can be said that the less active agent is for one Pfknze is needed, the more mature it is. In the The useful plants become practice. usually 1 to 2 weeks before harvest for defoliation

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treated. In some cases more than one treatment is desirable, especially if more severe Rain or wind occur soon after treatment, or when a cumulative effect is desired will. In order to avoid possible damage to one or the other plant species, it can then Even for an inexperienced practitioner, it may be desirable to use the defoliant first in proportion to use a small amount and then, if necessary, to follow up a second treatment later, when the effect of the first begins to be visible. The use of large surpluses beyond the minimum necessary for good defoliation can have a shock effect on the plant, associated with subsequent damage.

Indeed, the compositions of the present invention are distinct herbicides when used in Amounts are used which are significantly larger than the amounts necessary for defoliation, and If necessary, they can also be used with advantage for killing plants or germs (as in the case of Potatoes).

In addition to shortening the life cycle of plants, the new mixtures can also do that Delay seed germination in order to selectively increase the growth of certain unwanted plants to inhibit or prevent and to favor that of other plants, furthermore to the growth of tendrils in favor of fruiting to limit the harvest of the fruits of such tendril plants to facilitate or to encourage cuttings to develop stronger roots.

If defoliation is desired, the agent should be used in such an amount that at least the majority of the leaves become dry and / or fall off the living plant, but that no killing effect on the plant has yet set in. If, on the other hand, killing plants is the goal then a higher amount sufficient for the purpose must be used. In the latter case can, since the sensitivity of different plant species to the herbicidal effect varies greatly, a separate killing of the individual plant species may be expedient. This selective killing can still be varied by different sizing of the additives such as wetting agents in addition to the amplifiers will. , '

An exact explanation for how the above-described increase in effectiveness comes about is not known. The mentioned increase in effectiveness is, however, compulsory through the ones listed below Examples are shown, which are only intended to serve as an illustration, but in no way limit the invention.

, Example 1

Three series of aqueous solutions of the disodium salt of 3,6-endoxyhexahydro-o-phthalic acid were prepared, each series consisting of five solutions each containing the following concentrations of the active ingredient mentioned: 0.00125%. 0.0025 ° / ₀ ° 0.005 / o, 0.0075% and 0.01%. One of these rows did not contain an amplifier,

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each of the other two, on the other hand, also has a constant amount (0.05%) of an amplifier, in one series primary ammonium citrate and in the other secondary ammonium citrate. So moving 5, the proportions of the enhancer to the active ingredient within the limits of 5: 1 up to 40: i.

These solutions were applied to potted dwarf kidney bean plants that were about 20 cm high and on which the first three-leaved foliage was already large, but the second was still small. Separate groups of eight such plants each were immersed in the respective test solutions of the individual test series up to the first knot, whereupon the excess of solution was shaken off. About 2 ecm of the solution remained on each plant. Accordingly, the dosages of active ingredient on each plant, depending on the concentrations of the test solutions, were approximately 25, 50, 100, 150 and 200 μl. The dosage of enhancer was the same for each plant, 1000 μg. One group of plants was not treated with any solution and was used to control the rest.

Comparative tests using the enhancers alone, without the active additives, were also made

accomplished. For this purpose, groups of eight plants with o, O5 ° / ₀ aqueous solutions of the two amplifiers salts under the same conditions, treated as described above. All plants used for this test were of the same age and grown at the same time and under the same conditions. After the start of the experiment, the treated and the untreated samples were again exposed to the same growth conditions.

The observations made after 3 days are shown in Table I below, in which For the sake of simplicity, some abbreviations have been used, the meanings of which are as follows:

1 = easy
m = moderate
st = strong
vb = burned
vz = delayed

a = attached
K ¹ = untreated

Control plant
PB = primary leaves
DS = three-leaved
Saplings

The ones not and those only treated with the amplifiers Plants were without any noticeable impact. Similar control experiments were carried out at carried out in the following examples, and in no case was there any effect on the plants detected. . ■

Example 2

- Two series of aqueous solutions of disodium 3, 6-endoxyhexahydro-o-phthalate were prepared, each series of 5 solutions with the following concentrations of this active ingredient the composite was: 0.001%, 0.0025%, 0.005%. 0.01% and 0.015%.

The term 2e means that if there are two plants a single primary leaf has fallen off, 6 b means that in six plants, both primary leaves have fallen off are. The same abbreviations are also used in the tables below.

Amplifier as None ² 5, «g Table I. 100 / ig 150 ^ g 95 200 / d 30th as K PB ι vb;
DS like K PB m vb;
DS ι vz 4b; a PB m vb; 100
DS ι vz prim. Ammonium
⁴⁰ citrate PB ι vb;
DS like K Physiological effects 3b, 3e;
a PB m vb;
DS m vz; 6b, 2e;
a PB m vb;
DS st vz 8b;
DS st vz
105 sec. Ammonium
45 ^citrate ·· ■ ·. · ■ ·· PB ι vb;
DS like K Amount of active ingredients per plant ib, 3e;
a PB m vb;
DS ι vz 2b, ie;
a PB m vb;
DS m vz 5b, ie;
a PB m vb;
DS st vz 50 / ig as K 3b, ie;
a PB ι vb;
DS ι vz; ib;
a PB ι vb;
DS ι vz

One series of experiments contained no enhancer, the other one constant except for the active ingredient Amount (0.05%) of an enhancer, namely methyl primary ammonium citrate. It moved the ratio of the amount of enhancer to active ingredient between 3.3: 1 and 50: 1.

Separate groups of eight potted dwarf kidney bean plants in a state in which the first three-leaved foliage was still rolled up, were up to the first knots in the respective Test solutions of the individual rows immersed; the excess solution was shaken off. It approximate ecm solution remained on each plant. This resulted in the dosages of active ingredient per plant, depending on the concentrations of the

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additive solutions, with about 20, 50, 100, 200 and 300 fig. The dosage of enhancer was the same for all plants in the second series of experiments, namely approximately 1000 μg.

All of the plants used for this experiment were of the same age and time and under grew up under the same conditions. After immersion, the treated plants were inclusive the treated control plants, as well as the untreated plants, are again exposed to the same growth conditions as before. After 4 days the following observations were made:

Table II
Physiological effects

Concentrate ' without with prim. Methyl- tration of the amplifier ammonium citrate act. Duration part as K 2b, ι e; a PB m vb, 0.001 7o , DS ι vz as K 4b, 4e; a PB m vb, 0.0025 7 ₀ DS m vz 4b, ie; 8b; DS st vz 0.005 7o a PB mvb; DS ivz 6b, ie; 3b, 4e; 0.01% a PB m vb; a PB frozen; DS m vz DS st vz 6b, 2e; 3.b, 4e; 0.015% a PB frozen; a PB frozen DS m vz DS st vz

The term "frozen" used here indicates a condition of the leaves of a test plant to which the leaves were exposed to such rapid and drastic action that no separating layer was formed had formed. The leaves then cling tenaciously

^: to the plant, although the leaf and stem are dead and shriveled and show no tendency to fall off. From this it can be seen that the term "frozen" denotes a greater phytotoxic effect on the leaves than when the leaves actually fall off.

Example 3

Two series of aqueous solutions of disodium-3,6-endoxyhexahydro-o-phthalate were prepared, each series containing four solutions with the following concentrations of this active ingredient: 0.001%, 0.0025%, 0.005% ^and 0.01 % _v One series of the solutions contained no enhancer, the other, in addition to the active ingredient, a constant amount (0.05%) of an enhancer, namely diethylammonium primary citrate. The proportions of the amplifier to the active constituent were between 5: 1 and 50: 1.

Separate groups of ten potted dwarf kidney bean plants in the state in which the first three-leaved leaves were still rolled up were immersed in the respective test solutions in each row up to the first knots; excess solution was shaken off. About 2 ecm of solution remained on each plant. So ^: the dosages of active ingredient on each plant, depending on the solutions, were approximately ^: 20, 50, 100 and 200, ag. The dosage of enhancer in the plants treated with it were always the same, about 1000 μg. ''

All of the plants used for this experiment were of the same age and time and under grew up under the same conditions. After dipping, the treated plants were, including of the treated and untreated control plants, again using the same growth conditions exposed. The observations made after 3 days showed the following result:

Table ΙΪΙ Physiological Effects

Conc
tration of the
act. Duration
part without
amplifier Dimit prim, ethyl
ammonium citrate 0.001 7o PB ι vb;
DS like K 4b, 2e;
a PB m vb;
DS m vz 0.0025 7o ie;
a PB ι vb;
DS ι vz. iob;
DS st vz 0.005% 6b, 2e;
■ a PB m vb;
DS m vz iob;
DS st vz 0.01% io'b;
DS st vz 3b, 2e; a PB ge
froze; DS 3 plant
zen st damaged,
the other st vz

Example 4 '

Two series of aqueous solutions of disodium 3, 6-endoxyhexahydro-o-phthalate were prepared, each series containing four solutions with the following concentrations of the active ingredient: 0.001%, 0.002570, 0.005% ^{and <} i P, oi%. One series of the solutions did not contain an amplifier, the other in addition to the active ingredient contained a constant amount (0.05%) of primary triethanolammonium citrate as an amplifier. The ratio of the amount of enhancer to active ingredient was between 5: 1 and 50: 1.

Separate groups of 'eight potted' Dwarf kidney bean plants in the state in which the first three-leaved leaves were still rolled up, were immersed in the respective test solutions of the two rows up to the first knot; Excess solution was shaken off. About

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2 ecm of solution remained on each plant. So ν the dosage of active ingredient on each plant, depending on the concentrations of the solutions, was approximately 20, 50, 100 and 200 μ%, and that of enhancer was always approximately. iOoö /.tg..·: All plants used for these experiments were of the same age and grown in the same time and under the same conditions. The treated plants, as well as the treated and the untreated control plants, were exposed to the original growth conditions again after immersion,
the following was observed:

Table IV

After 3 days

25th 0.095% Physiological effects with prim. Triethanol Conc ammonium citrate tration of without act. Duration- 30 0.01% amplifier 6b, ie; a PB m vb; ²⁰ parts DS m vz 0.001% PB ι vb; 8b; DS ι vz DS st vz 0.0025% 4b, 2e; a PB m vb; 7b; a PB frozen; DS m vz DS st vz 5b, 2e; a PB m vb; 6b; a PB frozen; . DS st vz DS st vz 7b; ie; a PB frozen DS st vz

Example 5

Two series of aqueous solutions of disodium "3,6-endoxyhexahydro-o-phthalate" were prepared, each containing four solutions, with the following concentrations of the active ingredient: 0.00125%, 0.0025%> 0.005% and 0.0075 ° / _0. One series of the solutions contained no enhancer, the other in addition to the active ingredient contained a constant amount (0.05% / ₀ ) of ammonium lactate as enhancer.The ratio of enhancer to active ingredient was between 6.6 : 1 and 40: 1.

Separate groups of eight dwarf kidney bean plants each grown in pots in the state in which the first three-leaved leaves were still rolled up, were dipped to the first knots in the respective test solutions in each row; Excess solution was shaken off so that approximately 2 ecm of solution remained on each plant. This means that the dosage of active ingredient on each plant was approximately 25, 50, 100 and 150 μg, depending on the concentrations of the individual test solutions, and that of intensifiers in the second series was around 1000 μg each.

All plants and test series had the same age and were at the same time and under the same Conditions grew up; they were also after treatment, 'just like the treated and the untreated Control plants, again exposed to the same growing conditions. The observation after 4 days showed the following picture:

Table V

Physiological effects

Conc without With tration of amplifier Ammonia actate act. Duration share as K PB ι vb; 0.00125% DS like K as K PB m vb; 0.0025% DS ι vz PB ι vb; 4e; a PB st vb; 0.005% DS m vz DS st vz ib, 4e; 5b, ie; 0.0075% aPBmvb; a PB st vb; DS m vz DS st vz

The following amplifiers were also made in the same manner tested with the same results as above: methylammonium lactate, diethylammonium lactate, Triethanolammonium lactate, ammonium glycolate, methylammonium glycolate, diethylammonium glycolate and triethenol ammonium glycolate.

Example 6

Three series of aqueous solutions of disodium 3,6-endoxyhexahydro-o-phthalate were prepared, each series containing four solutions having the following concentrations of active ingredient: 0.00125 ° / ₀ , 0.0025 ° / o> 0.005% and 0.0075%. One row contained no enhancer, the other two in addition to the active ingredient a constant addition (0.05%) of an enhancer, one series acidic and the other neutral ammonium tartrate. The proportions of the enhancer to the active ingredient were each between 6.6: 1 and 40: 1.

Separate groups of sixteen dwarf kidney bean plants grown in pots in the state in which the first three-leaved leaves were still rolled up were immersed in the respective test solutions of the individual rows up to the first knots, whereupon the excess solution was shaken off. Around 2 ecm of solution remained on the plant. Accordingly, the doses of active ingredient, depending on the concentrations of the dipping liquids, were about 25, 50, 100 and 150 μg per plant, while that of intensifier in rows 2 and 3 was always about 1000 / ig.

All plants used for this series of experiments were of the same age and at the same time and under the same Conditions grew up; they also came after the treatment, just like those treated and untreated control plants, again in the same growth conditions. After 3 days they became observed for their condition, making the findings listed in Table VI.

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Table VI
Physiological effects

amplifier None 25th "G Amounts of active Components per plant 150 / ig PB ι vb;
DS like K 50 / ig 2b, 3e;
a PB m vb;
DS ι vz Sour Ammontartrat .. 2e;
a Pb m
DS ι vz vb; PB ι vb;
DS like K gb, 2e;
a PB frozen;
DS st vz Ammonium tartrate .... ib, 3e;
a PB m
DS ι vz vb; gb; 2e;
a PB st vb;
DS m vz iob, 6e;
a PB frozen;
DS st vz 8b, 5e;
a PB st vb;
DS m vz 100 ßg ib, ie;
a PB ι vb;
DS ι vz. 6b, 6e;
a PB frozen;
- DS st, vz 15b, ie;
a PB st vb;
DS st vz

Example 7

Three series of experimental aqueous solutions of disodium 3, 6-endoxyhexahydro-o-phthalate were prepared, each of which contained four solutions with the following concentrations of active ingredient: 0.00125%. 0.0025%. 0.005 ° / o ^un d 0.0075% · One solution contained no series amplifier, each of the two other than the active ingredient or a constant amount (0.05 ° / ₀₎ of an amplifier. The additives used as enhancers for these series of solutions were acidic and neutral ammonium malate. In these solutions, the ratio of enhancer to active ingredient was between 6.6: 1 and 40: i.

Separate groups of eight potted each Dwarf kidney bean plants in the zu

Table VII
Physiological effects

amplifier 25 / ig Amounts of active ingredients per plant 100 ßg 150 / d PBi vb;
DS like K 50 / ig PB ι vb;
DS ι vz 2 B; ,
a PB m vb;
DS m vz None PB ι vb;
DS ι vz PB ι vb;
DS like K 6b, ie;
a PB st vb;
DS m vz 8b;
DS st vz PB ι vb;
DS ι vz ib, ie;
a PB m vb;
DS ι vz 5b, 2e; ,
a PB m vb;
DS m vz 8b;
DS st vz acidic ammonium malate. 2 6 "
a PB m vb;
DS ι vz Ammonium malate

Example 8

Two series of aqueous solutions of bis (triethylammonium) -3, 6 -endoxyhexahydro-ophthalate were prepared, each of which consisted of five solutions with the following molar concentrations of this active ingredient: 0.000025, 0.00005, 0.0001, 0.00025 ^{un <} i 0) 005. The ^eme test series corresponds

stood in which the first three-leaved leaves were still rolled up to the first knots in the respective test solutions immersed, and the excess of solution was shaken off, whereby about 2 ecm of solution remained on the plant. Accordingly, depending on the concentration of the test solutions, the dosage of active ingredient per plant approximately 25, 50, 100 and 150, ag, of enhancer with rows 2 and 3 always about 1000 ^ g. All the plants used for these experiments were of the same age and in the same time and under the same Conditions grew up; they came after treatment as well as the untreated and the treated Control plants again in the same growing conditions. Those employed after 5 days Observations had the following result:

did not hold any reinforcer, the other in addition to the active ingredient still a constant amount (0.1%) Citric acid as an enhancer.

Separate groups of eight potted each Dwarf kidney bean plants in the state in which the first three-leaved leaves are still rolled up was up to the first knot in the

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individual test solutions immersed; the excess of the solutions was shaken off. Stayed like that about 2 edm of solution on each of the plants.

All plants used for this series of experiments were of the same age and grown at the same time and under the same conditions. After the immersion, the treated plants were, including the untreated control plants again the same growth conditions, (a o, i ° ₀ aqueous citric acid solution were / treated) and the untreated control plants, as exposed before. Observations after 8 days showed the following picture:

Table VIII.

•: Physiological effects

.Conc 25th 0.0001 30th 0.005 without With tration of amplifier citric acid act. Duration- ao ^parts 0.00025 i-like K PB vb; DS like K _; . 0.000025 molar as K 2b, ie; a PB m vb; 0.00005 DS m vz PB ι vb; 7b, ie; DS like K a PB st vb; DS st vz 2b, 3e; 8b; a PB m vb; DS st vz DS st vz " 8b; 7b, ie; a PB ge DS st vz froze; DS st vz

At the same time, a similar series of tests was carried out with disodium 3, 6-endoxyhexahydro-o-phthalate, once without an amplifier and the other time with citric acid as an amplifier, and one too another series with monosodium-3, 6-endoxyhexahydro-o-phthalate, again with and without citric acid as an amplifier.

These two sodium salts showed about the same effectiveness as the bis (triethylammonium) salt without an enhancer. Likewise, the activity of the sodium salts became about the same with citric acid Measures increased as with the bis (triethylammonium) salt.

Theoretically, the endoxy compounds can have three particular and different geometrically isomeric formulas, namely the exo-cis isomer, the endo-cis isomer and the trans isomer, as in the case of the ■ hexahydro compounds from Woodward and Baer, J. Am. Chem. Soc. 70, 1161 to 1166. Of these three isomers, the exo-cis isomer is preferred for the present process in view of its far greater effectiveness. Furthermore, the exo-cis isomer can be produced more cheaply and conveniently. The endoxy compounds mentioned in the above examples were of the exo-cis form. When the endoxy compounds are used in the form of the acids as such and / or in the form of their anhydrides, the aqueous solutions of the acids and / or the anhydrides probably contain unidentified acid and / or anhydride, in equilibrium with their ions. The same is likely to apply to some of their salts. ^;)

The alkylammonium salts of 3,6-endoxyhydroo-phthalic acids, like the salts of mono-, di- or trialkylammonium, preferably contain 1 to 12 carbon atoms in each alkyl radical, and the total number of the carbon atoms is preferably not more than 12. The alkanolammonium salts, such as those of the mono-, di- and Trialkanolamine, preferably have 2 to 3 carbon atoms in each alkanol radical. The mixed alkyl-alkanolammonium salts, like that of monoalkyl-monoalkanolammonium, dialkyl-monoalkariolammoniums or of the monoalkyl dialkanolamine preferably have 1 to 4 carbon atoms in each alkyl radical and 2 to 3 carbon atoms in every alkanol residue.

The neutral and acidic alkylammonium salts of the above-mentioned saturated, open-chain mono- and Dioxy mono-, di- and tricarboxylic acids with 2 to 6 carbon atoms, such as. B. the mono-, di- or trialkylammonium salts, preferably contain 1 to 4 carbon atoms in each alkyl radical.

The alkanolammonium salts, such as mono-, di- or trialkanolammonium salts, preferably have 2 to 3 carbon atoms in each alkanol residue. The mixed alkyl-alkanolammonium salts, such as those of the monoalkyl-monoalkanolamine, of the dialkyl-monoalkanqlamine or of the monoalkyl-dialkanolamine, mostly have ι to 4 carbon atoms in each alkyl radical and 2 to 3 carbon atoms in every alkanol residue. *

The following examples relate to both the active ingredients and the enhancers.

Examples of monoalkylammonium salts are the salts of monomethyl, monoethyl, monopropyl, Monobutyl, monoamyl, monohexyl, monooctyl, monononyl, monodecyl and monododecylamine and similar monoalkylammonium salts of the acids mentioned.

Examples of dialkylammonium salts are the salts of dimethyl, diethyl, dipropyl, dibutyl, Diamyl and dihexylamine, methylethylamine, ethylpropylamine, Propylbutylamine, amylhexylamine, methylundecylamine and like dialkylammonium salts of these acids.

Examples of trialkylammonium salts are those of trimethyl, triethyl, tripropyl and Tributylamine, methyl diethylamine, ethyldipropylamine, propyldibutylamine, methyldiamylamine, ethyldiamylamine, Methyläthylpropylamin, Äthylpropylbutylamin and similar salts with the mentioned Acids.

Examples of monoalkanolammonium salts are those of monoethanolamine and monopropanolamine and like salts of such acids.

Examples of dialcanic oil ammonium salts are the salts of diethanolamine and dipropanolamine, and ethanolpropanolamine and like salts of these acids.

Examples of trialkanolammonium salts are those of triethanol and tripropanolamine, ethanol dipropanolamine, Propanol diethanolamine and similar salts of these acids.

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Examples of monoalkyl-monoalkanolammoriium-

salts are those of methyl, ethyl, propyl and butylethanolamine, methyl, ethyl, propyl and Butylpropanolamine and similar salts of these acids.

Examples of dialkyl monoalkanolammonium salts are those of dimethyl, diethyl, dipropyl and Dibutylethanolamine, dimethyl-, diethyl-, dipropyl- and dibutylpropanolamine, methylethylethanolamine,

Methylethylpropanolamine, ethylpropylethanolamine,

ίο ethylpropylpropanolamine, propylbutylethanolamine, Propylbutylpropanolamine and similar salts of the acids mentioned.

Examples of monoalkyl-dialkanolammonium salts are the salts of methyl, ethyl, propyl and butyl

diethanolamine, methyl, ethyl, propyl and butyl

, .-; dipropanolamine, methyl-, ethyl-, propyl- and butylethanolpropanolamine and like salts of these acids. '■'

As stated above, the salts mentioned include both the acidic and the neutral and mixed salts, d. H. Salts with different cations.

The term "plant" as used here "relates affect all parts of the plant, such as the roots, stems, leaves, flowers, seeds and fruits. to the plants which are defoliated according to the present invention include, for. B. cotton, potatoes, Tomatoes and beans, such as soy and lima beans. Examples of harmful weeds, how to get rid of them The new mixtures that can be used are winches, chickweed, corn wheels, pine fronds, shepherd's purse, broad-leaved plantain, coltsfoot, ragwort, wolfsmüch, sorrel and wild Carrots.

The new mixtures are generally applicable as herbicides, either before or before the seeds emerge planting to control the weeds and after emergence to suppress the weeds in those crops that are only slightly or not at all attacked by the mixtures.

Claims (4)

PATENT CLAIMS: 1. Means for influencing plant growth, characterized in that they contain a compound which reacts in the presence of water acidic or neutral anion eh of 3, 6-endoxyhexahydroorthophthalic acid or 3, 6-endoxy-i, 2, 3, 6-tetrahydroorthophthalic acid supply, as well as an amplifier, for this a saturated, open-chain mono- or dioxy-mono-, di- or tricarboxylic acid with 2 to 6 carbon atoms bonded to one another or a salt of such an acid with one or more of the following bases: ammonium hydroxide, Alkyl amines, alkanol amines and mixed alkyl alkanol amines. 2. Composition according to claim 1, characterized in that the anions of the endoxyhydroorthophthalic acids have the exo-cis configuration. 3. Agent according to one of claims 1 or 2, characterized in that ammonium citrate as an amplifier, Ammonium tartrate, ammonium malate, or ammonium glycolate is used. 4. Agent according to one of the preceding claims, characterized in that it is a wetting agent as well as a humectant.