CA1168885A - Agents for regulating plant growth - Google Patents
Agents for regulating plant growthInfo
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- CA1168885A CA1168885A CA000418786A CA418786A CA1168885A CA 1168885 A CA1168885 A CA 1168885A CA 000418786 A CA000418786 A CA 000418786A CA 418786 A CA418786 A CA 418786A CA 1168885 A CA1168885 A CA 1168885A
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Abstract
ABSTRACT OF THE DISCLOSURE
Novel plant growth regulant composition comprising as an active ingredient at least one cycloalkanecarboxylic acid compound of the formula (1), in which (a) R is -NH2 and R is -OH;
(b) R is -NH-CHO and R is -OH or -OC2H5;
(c) R1 is -NH-COCH3 and R is -OCH3; or + -(d) R1 is -NH3-C1 and R is -OC2H5;
in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface active agent.
Novel plant growth regulant composition comprising as an active ingredient at least one cycloalkanecarboxylic acid compound of the formula (1), in which (a) R is -NH2 and R is -OH;
(b) R is -NH-CHO and R is -OH or -OC2H5;
(c) R1 is -NH-COCH3 and R is -OCH3; or + -(d) R1 is -NH3-C1 and R is -OC2H5;
in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface active agent.
Description
The present invention relates to the use of certain cycloalkane-carboxylic acid derivatives, which are known, as active compounds for regulating plant growth.
It has already been disclosed that (2-chloroethyl)-trimethylam-monium chloride has plant growth-regulating properties ~see United States Patent Specification 3,156,554). However, the activity of this substance is not always completely satisfactory, especially when low amounts are used.
It has furthermore been disclosed that a product, commercially available under the name "Off-Shoot-T", based on fatty alcohols with 6, 8, 10 and 12 carbon atoms can be employed for regulating plant growth, in particular for suppressing the growth of side shoots in tobacco (see Farm. Chem. Handbook 1975, Meister Publishing Co., Willoughby, Ohio, 1975 and Pesticide Dictionary D 147). Nevertheless, in some cases, especially when low amo~mts are used, the activity of this product also leaves something to be dèsired.
It is also already known that 2-chloroethylphosphonic acid can be used as a plant growth regulator ~see German Offenlegungsschrift (German Published Specification) 2,050,245). However, its action is also not completely satisfactory when low amounts are used.
It has now been found that cycloalkane-carboxylic acid derivatives of the general formula ~Rl ~r)7 V C-R
O
in which (a) Rl is -~l2 and R is -OH;
(b) Rl ls -~f-CH0 and R is -aH or -OC2H5;
(c) Rl is NH~COCH3 and R ls ~CH3; or ~ d) Rl is -NH30Cl and R is -OC2H5;
are ~er~ suitable for regulating plant gro~th.
Accordingly, the present invention provides a plant growth-regulating composition containing as active ingredient a compound o the formula (I) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface~active agent.
The invention also provides a method of regulating the growth of plants which comprises applying to the plants, or to a habitat thereof, a compound of the formula (I) alone or in the form of a composition containing as active ingredient a compound of the present invention in admixture ~ith a diluent or carrier.
The compounds of the formula (I) are known (see Liebigs Ann. Chem. 1~73, 611~618; Monatsh~ ~hem. 103, 288 291 (1972), and Nature 179, 360~361 (1957).
The compounds used in the compositions according to the Z0 present invention engage in the metabolism of plants and can therefore be employed as growth regulatorsO
Experience to date of the mode of action of plant growth regulators has shown that an active compound can exert one or several different actions on plants. The actions of the compounds depend essen~
tially on the point in time at which they are used, relative to the stage of development of the seed or of the plant, and on the amounts of ~ 3 6~5 active compound applied to the plants or their environment and the way in which the compounds are applied. In every case, growth regulators are intended positively to influence the crop plants in the desired manner.
Plant growth-regulating compounds can be employed, for example, to inhibit vegetative plant growth. Such inhibition of growth is inter alia of economic interest in the case of grasses since, by repressing the growth of grass, it is possible, for example, to reduce the frequency of cutting the grass in ornamental gardens, parks and sports grounds or at verges The inhibltion of growth of herbaceous and woody plants at verges and in the vicinity of overland pipelines or, quite generally, in areas in which heavy growth is ~mdesired~ is also of imporkance.
The use of growth regulators to inhibit the growth in length of cereals is also important, since by shortening the stem the danger of lodging of the plants before harvesting is reduced or completely eliminated. Furthermore, growth regulators can strengthen the stem of cereals, which can counteract lodging.
In the case of many crop plants, inhibition of the vegetative growth permits denser planting of the crop, so that a greater yield per area of ground can be achieved.
A~further mechanism of increasing the yield by means of growth inhibitors is based on the fact that the nutrients benefit blossoming and fruit formation to a greater extent, whilst vegetative growth is restricted.
Promotion of vegetative growth can also frequently be achieved with growth regulators. This is of great utility if it is the vegetative ~ 3 ~85 parts of the plants which are harvested. Promoting the vegetative growth can, however, also simultaneously lead to a promotion of gener-ative growth, so that, for example, more fruit, or larger fruit, is formed.
Increases in yield can in some cases also be achieved by affecting the plant metabolism, without noticeable changes in vegetative growth. Growth regulators can furthermore produce a change in the com-position of the plants so as to bring about better quality of the harvested products. Thus it is possible, for example, to increase the content of sugar in sugar beet, sugar cane, pineapples and citrus fruit or to increase the protein content in soya or cereals.
Parthenocarpous fruit can be formed under the influence of growth regulators. Furthermore, the gender of the flowersi~can be influenced.
Using growth regulators it is also possible favourably to influence the production or the efflux of secondary plant materials.
The s~imulation of latex flow in rubber trees may be mentioned as an example.
During the growth of the plant, lateral branching can also be increased, by using growth regulators, through chemical breaking of the apical dominance. There is interest in this, for example, in the case of plant propagation by cuttings. However, it is also possible to inhibit the growth of side shoots, for example to prevent the formation of side shoots in tobacco plants after decapitation and thus to promote leaf growth.
The amount of leaf on plants can be controlled, under the ... .
influence of grow-th regulators, so that defoliation of the plants at a desired point in time is achieved. Such defloiation is of interest to facilitate mechanical harvesting, for example of grapes or cotton, or to lower the transyiration at a point in time at which the plant is to be transplanted Premature shedding of fruit can be prevented by the use of growth regulators. However, it is also possible to promote the shedding of fruit - for example in the case of table fruit - in the sense of a chemical thinning out, up to a certain degree. Growth regulators can also be used to reduce the force required ko detach the fruit from crop plants at harvest time so as to permit mechanical harvesting of the plants or facilitate manual harvesting.
Using growth regulators it is furthermore possible to achieve an acceleration or retardation of ripening of the harvest product, before or after harvesting. This is of particular advantage since it is thereby possible to achieve optimum adaptation to market requirements.
Purthermore, growth regulators can at times improve the coloration of fruit. In addition, concentrating the ripening within a certain period of time is also achievable with the aid of growth regulators. This provides the preconditions for being able to carry out complete mechanical or manual harvesting in only a single pass, for example in the case of tobacco, tomatoes or coffee.
Using growth regulators it is also possible to influence the latent period of seeds or buds of plants, that is to say the endogenic annual rhythm, so that the plants, such as, for example, pineapple or decorative plants in nurseries, germinate, shoot or blossom at a time at 7 1 ~8~
which they normally show no readiness to do so.
Using growth regulators it is also possible to achieve a delay in the shooting of buds or the germination of seeds, for example to avoid damage by late frosts in regions w]lere frost is a hazard.
Growth regulators can also produce halophilism in crop plants.
This provides the preconditions for being able to cultivate plants on soils containing sa~t.
Using growth regulators, it is also possible to induce frost resistance and drought resistance in plants.
The preferrcd time of application of the growth regulators depends on the climatic and vegetative circumstances.
The foregoing description should not be taken as implying that each of the compounds can exhibit all of the described effects on plants. The effect exhibited by a compound in any particular set of circumstances must be determined empirically.
The active c~mpounds can ke cunverted into the customary formu-lations, s.uch as solutions, emulsion~, we~takle powders~ suspensions, powders, dusting agents, foams, pastes, soluble powders, granules, aerosols, sus-pension_emulsion co~centrates, s~ed~reatment powders, natural and synthetic ~0 materials impregnated with active compound and very fine capsules in polymeric substances,coating compositions for use on seed, as well as ULV cold mist and warm mist formulations.
These formulations may be produced in known manner, for example ~y mixing the active compounds with extenders, that is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, that is to say emulsifying agents and/or dispersing ~ ~ 68~5 agents and/or foam-forming agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solventsO
As liquid diluents or carriers, especially solvents7 there are suitable in the main, aromatic hydrocarbons, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydro-carbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic or alicyclic hydrocarbons, such as cyclohexane or paraffills, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, as well as water.
By liquefied gaseous diluents or carriers are meant liquids which ~ould be gaseous at normal temperature and under normal pressure, for exa~ple aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
As solid carriers there may be used ground natural miner~ls, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates. As solid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maiæe cobs and tobacco stalks.
As emulsifying and/or foam forming agents there may be used non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, 8 ~
polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysis products. Dispersing agents include~ for example, lignin sulphite waste liquors and methylcellulase.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvin~l acetate, can be used in the formulations.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue9 and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zincO
The formulations in general contain from 0,1 to 95 per cent by weight of active compound, preferably from 0.5 to ~0 per cent by weightO
The active compounds, according to the invention, can be present in the formulations as a mixture with other known active compounds, such as fungicides, insecticides; acaricides and herbicides, and also as mix-tures with fertilisers and other gro~th regulatorsO
The active compounds can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders, pastes, soluble powders, dusting agents and granules.
They may be used in the customary manner, for example by watering, spraying, atomising, scattering, dusting, foaming and gassing. Furthermore it is possible to apply the active compounds in accordance ~ith the ultra~low v~lume method, to spread the active compound preparation or the active i J ~85 compound itself on plants or partsf o plants or to inject the active compound preparation or the active compound itself into the soil. It is also possible to treat the seeds of plants.
The active compound concentrations can be varied within a substantial range. In general, 0.01 to 50 kg, preferably 0.05 to 10 kg, of the active compound are employed per hectare of soil surface.
It will be seen that the usual methods or providing a harvested crop may be improved by the present inventionO
The plant-growth-regulating activity of the compounds used in the compositions of this invention is illustrated by the following biotest Fxample5O
In these Examples, the compounds used in the compositions according to the present invention are each identified by the number ~given in brackets) of the corresponding preparative Example or identifying information7 which will be found later in this specification.
The known comparison compounds are identified as follows:
(A) = "O-ff-Shoot-T"
~ B) = Cl-CH2-CH~-N(CH3)3Cl e ~ C) - Cl-CH2CH2~(OH)2 ~
Inhibition of gro~th of barley Solvent: 30 parts by weight of dimethylformamide ~mulsifier: 1 part by weight of po~yoxyethrlene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier and the mixture was made up to the desired concentration with water.
~ 1 6~85 Barley plants were grown to the 2~1eaf stage in a greenhouse.
In this stage, the plants were sprayed with the preparations of active compound until dri.pping wetO After 3 weeks, the additional growth was measured on all plants and the inhibition of growth in % of the additional growth of the control plants wa$ calculated. 100% meant that growth had stopped and 0% denoted a growth correspondi.ng to that of the control plants.
The active compounds, active compound concentrations and results can be seen from the table which follo~sO
~-Inhibition of growth of barley Active Active compound Inhibition of compound concentration in % growth in %
O
(control) ~3) 0O05 30 Inhibition of growth of wheat Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene sorbitan monolaurate ~0 To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed ~ith the stated amounts of solvent and emulsifier and the mixture was made up to the desired concentrations with water.
~heat plants were grown to the 2~1eaf stage in a greenhouse.
In this stage, the plants were sprayed with the preparations of active compound until dripping wetO After 3 weeks, the additional growth was measured on all plants and the inhibition of growth in % of the additional ~ :# ~8~5 growth of the control plants was calculated. 100% meant that growth had stopped and 0% denoted a gro~th corresponding to that of the control plants.
The active compounds, active compound concentrations and results can be seen from the table which follows..
T~BLE tII) Inhibition of_growth of wheat Active Active compound Inhibition of compound _ concen_ration in % growth in %
_ .
O
~control~
(3~ 0O05 ~5 ~11) 0O05 30 Inhibition of growth of soya beans Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part ~y weight of polyoxyethylene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed ~ith the stated amounts of solvent and emulsifier and the mixture was made up to the des~red concentration with water.
Soya bean plants were grown in a greenhouse until the first secondary leaf had unfolded completely. In this stage, the plants were sprayed ~ith the preparations of active compound until dripping wet. After 3 ~eeks, the additional growth was measured on all the plants and the inhibition of growth in % of the additional growth of the control plants ~as calculated. 100% meant that gro~th had stopped and 0% denoted a growth corres.ponding to that of the control plantsO
~he active compounds, active compound concentrations an~
. :
. ' ' 7 1 ~ 5 res,ults can ~e seen from the table which follo~sO
Inhibition of growth of soya beans Active Active compound Inhibition o compound concentration_in % growth in %
--O
~control~
(B) 0.05 0 (3~ 0O05 75 *
* Plants exhibited a dark green coloration Example ~I ~
Stimulation of ethylene biosynthesis.
Solvent: 30 parts by weight of dimethylformamide Emulsifier: l part by weight of polyoxyethylene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed ~ith the stated amounts of solvent and emulsifier and the mixture was made up to the desired concentration with water.
Pieces of leaf of identical s,ize ~ere punched from soya bean leaves. A constant number of pieces of leaf was incubated for l hour in Petri dishes which were filled with lO ml of the active compound preparations ~r with correspond-ing control solutions ~ithout active compounds, There-after, the pieces of leaf were introduced into vessels which were closed air-tight, together with l ml of the particular preparation of active compound or control solution. After 24 hours the ethylene which had collected in the ves~els ~as determined b~ customary methads o detectionO The -12_ , .
: .
evolution of eth~lene from the pleces of leaf treated ~ith the preparations of active compound was compared with the evolution o ethylene of the control 5 .
In the table which follows:
o denotes no action denotes sligh~ stimulation af ~th~lene biosynthesis denotes moderate stimulation of ethylene biosynthesis denotes high stimulation of eth~lene biosynthesis This tes~ was particularly sultable or illustraking the growth-10~egulating properties of the compounds according to the invention.
The plant hormone eth~lene affects numerous processes during thedevelopment of the plantsO An increase in eth~lene biosynthesis, such as can be achieved with the substances according to the invention, makes it possible to control these processes. The following may be mentioned here as examples in which there is, in particular, commercial interes*- detach-ment of fruit, acceleration of ripening of fruit and leaves, induction of flowering, germination of seeds, thinning-out of fruit, stimulation of latex flux, for example in Hevea, influencing of gender and inhibition of growth, for example also to prevent the lodging of cereals.
2QThe active compounds and the results can be seen from the table which followsO
~5~
Stimulation of ethylene biosynthesis Active Active compound Action com~ound concentration in %
~ o ccontrol) (~) O.OQl ' .
, I :q 6~885 TABLE ~ V~ cont'd Active Active compoundAction com~ound concentration in %
(3) 0.001 ~+-~
(11) 001 -~
~) 0~ 001 +~+
(19) ~. 001 +++
Preparative Example NH-CHO
~ IC~ I (3) o 8.36 g (0.05 mole) of potassium a formylamino-cyclopropanecar-box~late were dissolyed in 20 ml of water, and 5 g (0.05 mole) of concentra~ed hydrochloric acid were added at 0C. The mixture was ieft to stand at 5C overnight. After filtering off the precipitate and drying it, 5.2 g ~80% of theory) of ~ formylamino-cyclopropanecarboxylic acid were obtained in the form of colourless crystals. Melting point: 189Co The other active compounds used in the compositions of the invention are identified by the following numbers:
20Com,pound R Rl 11 OC2H5 NHCHO b. pt. 110 at 0.1 mbars 19 OH MH2 m. pto 220 ~C2H5 ~H3Cle m~ pt. 108 23a OCH3 NHCOGH3
It has already been disclosed that (2-chloroethyl)-trimethylam-monium chloride has plant growth-regulating properties ~see United States Patent Specification 3,156,554). However, the activity of this substance is not always completely satisfactory, especially when low amounts are used.
It has furthermore been disclosed that a product, commercially available under the name "Off-Shoot-T", based on fatty alcohols with 6, 8, 10 and 12 carbon atoms can be employed for regulating plant growth, in particular for suppressing the growth of side shoots in tobacco (see Farm. Chem. Handbook 1975, Meister Publishing Co., Willoughby, Ohio, 1975 and Pesticide Dictionary D 147). Nevertheless, in some cases, especially when low amo~mts are used, the activity of this product also leaves something to be dèsired.
It is also already known that 2-chloroethylphosphonic acid can be used as a plant growth regulator ~see German Offenlegungsschrift (German Published Specification) 2,050,245). However, its action is also not completely satisfactory when low amounts are used.
It has now been found that cycloalkane-carboxylic acid derivatives of the general formula ~Rl ~r)7 V C-R
O
in which (a) Rl is -~l2 and R is -OH;
(b) Rl ls -~f-CH0 and R is -aH or -OC2H5;
(c) Rl is NH~COCH3 and R ls ~CH3; or ~ d) Rl is -NH30Cl and R is -OC2H5;
are ~er~ suitable for regulating plant gro~th.
Accordingly, the present invention provides a plant growth-regulating composition containing as active ingredient a compound o the formula (I) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface~active agent.
The invention also provides a method of regulating the growth of plants which comprises applying to the plants, or to a habitat thereof, a compound of the formula (I) alone or in the form of a composition containing as active ingredient a compound of the present invention in admixture ~ith a diluent or carrier.
The compounds of the formula (I) are known (see Liebigs Ann. Chem. 1~73, 611~618; Monatsh~ ~hem. 103, 288 291 (1972), and Nature 179, 360~361 (1957).
The compounds used in the compositions according to the Z0 present invention engage in the metabolism of plants and can therefore be employed as growth regulatorsO
Experience to date of the mode of action of plant growth regulators has shown that an active compound can exert one or several different actions on plants. The actions of the compounds depend essen~
tially on the point in time at which they are used, relative to the stage of development of the seed or of the plant, and on the amounts of ~ 3 6~5 active compound applied to the plants or their environment and the way in which the compounds are applied. In every case, growth regulators are intended positively to influence the crop plants in the desired manner.
Plant growth-regulating compounds can be employed, for example, to inhibit vegetative plant growth. Such inhibition of growth is inter alia of economic interest in the case of grasses since, by repressing the growth of grass, it is possible, for example, to reduce the frequency of cutting the grass in ornamental gardens, parks and sports grounds or at verges The inhibltion of growth of herbaceous and woody plants at verges and in the vicinity of overland pipelines or, quite generally, in areas in which heavy growth is ~mdesired~ is also of imporkance.
The use of growth regulators to inhibit the growth in length of cereals is also important, since by shortening the stem the danger of lodging of the plants before harvesting is reduced or completely eliminated. Furthermore, growth regulators can strengthen the stem of cereals, which can counteract lodging.
In the case of many crop plants, inhibition of the vegetative growth permits denser planting of the crop, so that a greater yield per area of ground can be achieved.
A~further mechanism of increasing the yield by means of growth inhibitors is based on the fact that the nutrients benefit blossoming and fruit formation to a greater extent, whilst vegetative growth is restricted.
Promotion of vegetative growth can also frequently be achieved with growth regulators. This is of great utility if it is the vegetative ~ 3 ~85 parts of the plants which are harvested. Promoting the vegetative growth can, however, also simultaneously lead to a promotion of gener-ative growth, so that, for example, more fruit, or larger fruit, is formed.
Increases in yield can in some cases also be achieved by affecting the plant metabolism, without noticeable changes in vegetative growth. Growth regulators can furthermore produce a change in the com-position of the plants so as to bring about better quality of the harvested products. Thus it is possible, for example, to increase the content of sugar in sugar beet, sugar cane, pineapples and citrus fruit or to increase the protein content in soya or cereals.
Parthenocarpous fruit can be formed under the influence of growth regulators. Furthermore, the gender of the flowersi~can be influenced.
Using growth regulators it is also possible favourably to influence the production or the efflux of secondary plant materials.
The s~imulation of latex flow in rubber trees may be mentioned as an example.
During the growth of the plant, lateral branching can also be increased, by using growth regulators, through chemical breaking of the apical dominance. There is interest in this, for example, in the case of plant propagation by cuttings. However, it is also possible to inhibit the growth of side shoots, for example to prevent the formation of side shoots in tobacco plants after decapitation and thus to promote leaf growth.
The amount of leaf on plants can be controlled, under the ... .
influence of grow-th regulators, so that defoliation of the plants at a desired point in time is achieved. Such defloiation is of interest to facilitate mechanical harvesting, for example of grapes or cotton, or to lower the transyiration at a point in time at which the plant is to be transplanted Premature shedding of fruit can be prevented by the use of growth regulators. However, it is also possible to promote the shedding of fruit - for example in the case of table fruit - in the sense of a chemical thinning out, up to a certain degree. Growth regulators can also be used to reduce the force required ko detach the fruit from crop plants at harvest time so as to permit mechanical harvesting of the plants or facilitate manual harvesting.
Using growth regulators it is furthermore possible to achieve an acceleration or retardation of ripening of the harvest product, before or after harvesting. This is of particular advantage since it is thereby possible to achieve optimum adaptation to market requirements.
Purthermore, growth regulators can at times improve the coloration of fruit. In addition, concentrating the ripening within a certain period of time is also achievable with the aid of growth regulators. This provides the preconditions for being able to carry out complete mechanical or manual harvesting in only a single pass, for example in the case of tobacco, tomatoes or coffee.
Using growth regulators it is also possible to influence the latent period of seeds or buds of plants, that is to say the endogenic annual rhythm, so that the plants, such as, for example, pineapple or decorative plants in nurseries, germinate, shoot or blossom at a time at 7 1 ~8~
which they normally show no readiness to do so.
Using growth regulators it is also possible to achieve a delay in the shooting of buds or the germination of seeds, for example to avoid damage by late frosts in regions w]lere frost is a hazard.
Growth regulators can also produce halophilism in crop plants.
This provides the preconditions for being able to cultivate plants on soils containing sa~t.
Using growth regulators, it is also possible to induce frost resistance and drought resistance in plants.
The preferrcd time of application of the growth regulators depends on the climatic and vegetative circumstances.
The foregoing description should not be taken as implying that each of the compounds can exhibit all of the described effects on plants. The effect exhibited by a compound in any particular set of circumstances must be determined empirically.
The active c~mpounds can ke cunverted into the customary formu-lations, s.uch as solutions, emulsion~, we~takle powders~ suspensions, powders, dusting agents, foams, pastes, soluble powders, granules, aerosols, sus-pension_emulsion co~centrates, s~ed~reatment powders, natural and synthetic ~0 materials impregnated with active compound and very fine capsules in polymeric substances,coating compositions for use on seed, as well as ULV cold mist and warm mist formulations.
These formulations may be produced in known manner, for example ~y mixing the active compounds with extenders, that is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, that is to say emulsifying agents and/or dispersing ~ ~ 68~5 agents and/or foam-forming agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solventsO
As liquid diluents or carriers, especially solvents7 there are suitable in the main, aromatic hydrocarbons, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydro-carbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic or alicyclic hydrocarbons, such as cyclohexane or paraffills, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, as well as water.
By liquefied gaseous diluents or carriers are meant liquids which ~ould be gaseous at normal temperature and under normal pressure, for exa~ple aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
As solid carriers there may be used ground natural miner~ls, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates. As solid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maiæe cobs and tobacco stalks.
As emulsifying and/or foam forming agents there may be used non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, 8 ~
polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysis products. Dispersing agents include~ for example, lignin sulphite waste liquors and methylcellulase.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvin~l acetate, can be used in the formulations.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue9 and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zincO
The formulations in general contain from 0,1 to 95 per cent by weight of active compound, preferably from 0.5 to ~0 per cent by weightO
The active compounds, according to the invention, can be present in the formulations as a mixture with other known active compounds, such as fungicides, insecticides; acaricides and herbicides, and also as mix-tures with fertilisers and other gro~th regulatorsO
The active compounds can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders, pastes, soluble powders, dusting agents and granules.
They may be used in the customary manner, for example by watering, spraying, atomising, scattering, dusting, foaming and gassing. Furthermore it is possible to apply the active compounds in accordance ~ith the ultra~low v~lume method, to spread the active compound preparation or the active i J ~85 compound itself on plants or partsf o plants or to inject the active compound preparation or the active compound itself into the soil. It is also possible to treat the seeds of plants.
The active compound concentrations can be varied within a substantial range. In general, 0.01 to 50 kg, preferably 0.05 to 10 kg, of the active compound are employed per hectare of soil surface.
It will be seen that the usual methods or providing a harvested crop may be improved by the present inventionO
The plant-growth-regulating activity of the compounds used in the compositions of this invention is illustrated by the following biotest Fxample5O
In these Examples, the compounds used in the compositions according to the present invention are each identified by the number ~given in brackets) of the corresponding preparative Example or identifying information7 which will be found later in this specification.
The known comparison compounds are identified as follows:
(A) = "O-ff-Shoot-T"
~ B) = Cl-CH2-CH~-N(CH3)3Cl e ~ C) - Cl-CH2CH2~(OH)2 ~
Inhibition of gro~th of barley Solvent: 30 parts by weight of dimethylformamide ~mulsifier: 1 part by weight of po~yoxyethrlene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier and the mixture was made up to the desired concentration with water.
~ 1 6~85 Barley plants were grown to the 2~1eaf stage in a greenhouse.
In this stage, the plants were sprayed with the preparations of active compound until dri.pping wetO After 3 weeks, the additional growth was measured on all plants and the inhibition of growth in % of the additional growth of the control plants wa$ calculated. 100% meant that growth had stopped and 0% denoted a growth correspondi.ng to that of the control plants.
The active compounds, active compound concentrations and results can be seen from the table which follo~sO
~-Inhibition of growth of barley Active Active compound Inhibition of compound concentration in % growth in %
O
(control) ~3) 0O05 30 Inhibition of growth of wheat Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene sorbitan monolaurate ~0 To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed ~ith the stated amounts of solvent and emulsifier and the mixture was made up to the desired concentrations with water.
~heat plants were grown to the 2~1eaf stage in a greenhouse.
In this stage, the plants were sprayed with the preparations of active compound until dripping wetO After 3 weeks, the additional growth was measured on all plants and the inhibition of growth in % of the additional ~ :# ~8~5 growth of the control plants was calculated. 100% meant that growth had stopped and 0% denoted a gro~th corresponding to that of the control plants.
The active compounds, active compound concentrations and results can be seen from the table which follows..
T~BLE tII) Inhibition of_growth of wheat Active Active compound Inhibition of compound _ concen_ration in % growth in %
_ .
O
~control~
(3~ 0O05 ~5 ~11) 0O05 30 Inhibition of growth of soya beans Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part ~y weight of polyoxyethylene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed ~ith the stated amounts of solvent and emulsifier and the mixture was made up to the des~red concentration with water.
Soya bean plants were grown in a greenhouse until the first secondary leaf had unfolded completely. In this stage, the plants were sprayed ~ith the preparations of active compound until dripping wet. After 3 ~eeks, the additional growth was measured on all the plants and the inhibition of growth in % of the additional growth of the control plants ~as calculated. 100% meant that gro~th had stopped and 0% denoted a growth corres.ponding to that of the control plantsO
~he active compounds, active compound concentrations an~
. :
. ' ' 7 1 ~ 5 res,ults can ~e seen from the table which follo~sO
Inhibition of growth of soya beans Active Active compound Inhibition o compound concentration_in % growth in %
--O
~control~
(B) 0.05 0 (3~ 0O05 75 *
* Plants exhibited a dark green coloration Example ~I ~
Stimulation of ethylene biosynthesis.
Solvent: 30 parts by weight of dimethylformamide Emulsifier: l part by weight of polyoxyethylene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed ~ith the stated amounts of solvent and emulsifier and the mixture was made up to the desired concentration with water.
Pieces of leaf of identical s,ize ~ere punched from soya bean leaves. A constant number of pieces of leaf was incubated for l hour in Petri dishes which were filled with lO ml of the active compound preparations ~r with correspond-ing control solutions ~ithout active compounds, There-after, the pieces of leaf were introduced into vessels which were closed air-tight, together with l ml of the particular preparation of active compound or control solution. After 24 hours the ethylene which had collected in the ves~els ~as determined b~ customary methads o detectionO The -12_ , .
: .
evolution of eth~lene from the pleces of leaf treated ~ith the preparations of active compound was compared with the evolution o ethylene of the control 5 .
In the table which follows:
o denotes no action denotes sligh~ stimulation af ~th~lene biosynthesis denotes moderate stimulation of ethylene biosynthesis denotes high stimulation of eth~lene biosynthesis This tes~ was particularly sultable or illustraking the growth-10~egulating properties of the compounds according to the invention.
The plant hormone eth~lene affects numerous processes during thedevelopment of the plantsO An increase in eth~lene biosynthesis, such as can be achieved with the substances according to the invention, makes it possible to control these processes. The following may be mentioned here as examples in which there is, in particular, commercial interes*- detach-ment of fruit, acceleration of ripening of fruit and leaves, induction of flowering, germination of seeds, thinning-out of fruit, stimulation of latex flux, for example in Hevea, influencing of gender and inhibition of growth, for example also to prevent the lodging of cereals.
2QThe active compounds and the results can be seen from the table which followsO
~5~
Stimulation of ethylene biosynthesis Active Active compound Action com~ound concentration in %
~ o ccontrol) (~) O.OQl ' .
, I :q 6~885 TABLE ~ V~ cont'd Active Active compoundAction com~ound concentration in %
(3) 0.001 ~+-~
(11) 001 -~
~) 0~ 001 +~+
(19) ~. 001 +++
Preparative Example NH-CHO
~ IC~ I (3) o 8.36 g (0.05 mole) of potassium a formylamino-cyclopropanecar-box~late were dissolyed in 20 ml of water, and 5 g (0.05 mole) of concentra~ed hydrochloric acid were added at 0C. The mixture was ieft to stand at 5C overnight. After filtering off the precipitate and drying it, 5.2 g ~80% of theory) of ~ formylamino-cyclopropanecarboxylic acid were obtained in the form of colourless crystals. Melting point: 189Co The other active compounds used in the compositions of the invention are identified by the following numbers:
20Com,pound R Rl 11 OC2H5 NHCHO b. pt. 110 at 0.1 mbars 19 OH MH2 m. pto 220 ~C2H5 ~H3Cle m~ pt. 108 23a OCH3 NHCOGH3
Claims (16)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A plant growth regulating composition containing as active ingredient at least one cyclopropanecarboxylic acid derivative of the formula (I) wherein (a) R1 is -NH2 and R is -OH;
(b) R1 is -NH-CHO and R is -OH or -OC2H5;
(c) R1 is -NH-COCH3 and R is -OCH3; or + -(d) R1 is -NH3.C1 and R is -OC2H5;
in admixture with a solid or liquified gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface active agent.
(b) R1 is -NH-CHO and R is -OH or -OC2H5;
(c) R1 is -NH-COCH3 and R is -OCH3; or + -(d) R1 is -NH3.C1 and R is -OC2H5;
in admixture with a solid or liquified gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface active agent.
2. A composition according to claim 1 characterised in that it contains 0.1 to 95% of active ingredient by weight.
3. A composition according to claim 1 or 2 wherein the active ingredient is the compound of formula (I) in which R1 is -NH2 and R is -OH,
4. A composition according to claim 1 or 2 wherein the active ingredient is the compound of formula (I) in which R1 is -NH-CHO and R is -OH.
5. A composition according to claim 1 or 2 wherein the active ingredient is the compound of formula (I) in which R1 is -NH-CHO and R is -OC2H5.
6. A composition according to claim 1 or 2 wherein the active ingredient is the compound of formula (I) in which R1 is -NH-COCH3 and R is -OCH3.
7. A composition according to claim 1 or 2 wherein the active ingredient is the compound of formula (I) in whlch R1 is + --NH3.C1 and R is -OC2H5.
8. A method of regulating the growth of plants characterised in that there is applied to the plants, or to a habitat thereof, a compound of the formula (I) defined in claim 1.
9. A method according to claim 8 wherein the compound is applied in the form of a composition containing said compound as active ingredient in admixture with a suitable diluent or carrier.
10. A method according to claim 8 or 9 wherein the compound is applied to an area of plant cultivation in an amount of 0.01 to 50 kg per hectare.
11. A method according to claim 9 wherein the compound is applied to an area of plant cultivation in an amount of 0.05 to 10 kg per hectare.
12. A method according to claim 8, 9 or 11 wherein the compound is the compound of formula (I) in which R1 is -NH2 and R is -OH.
13. A method according to claim 8, 9 or 11 wherein the compound is the compound of formula (I) in which R1 is -NH-CHO
and R is -OH.
and R is -OH.
14. A method according to claim 8, 9 or 11 wherein the compound is the compound of formula (I) in which R1 is -NH-CHO
and R is -OC2H5.
and R is -OC2H5.
15. A method according to claim 8, 9 or 11 wherein the compound is the compound of formula (I) in which R1 is -NH-COCH3 and R is -OCH3.
16. A method according to claim 8, 9 or 11 wherein the + -compound is the compound of formula (I) in which R1 is -NH3.C1 and R is -OC2H5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000418786A CA1168885A (en) | 1978-06-03 | 1982-12-30 | Agents for regulating plant growth |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782824517 DE2824517A1 (en) | 1978-06-03 | 1978-06-03 | AGENTS FOR REGULATING PLANT GROWTH |
| DEP2824517.2 | 1978-06-03 | ||
| DE19792906507 DE2906507A1 (en) | 1979-02-20 | 1979-02-20 | Plant growth regulating compsn. - contg. alpha amino cyclo:alkanoic acid derivs., e.g. for dwarfing cereals |
| DEP2906507.4 | 1979-02-20 | ||
| CA000328930A CA1162559A (en) | 1978-06-03 | 1979-06-01 | Derivatives of 1-aminocyclopropane carboxylic acid |
| CA000418786A CA1168885A (en) | 1978-06-03 | 1982-12-30 | Agents for regulating plant growth |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1168885A true CA1168885A (en) | 1984-06-12 |
Family
ID=27426153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000418786A Expired CA1168885A (en) | 1978-06-03 | 1982-12-30 | Agents for regulating plant growth |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1168885A (en) |
-
1982
- 1982-12-30 CA CA000418786A patent/CA1168885A/en not_active Expired
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