Note: Descriptions are shown in the official language in which they were submitted.
8 S
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,
-7-
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
--10-
~ :# ~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~
11-
. :
. ' '
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
-13
' .
,
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
-14-
