Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
~79L~%:~
The present invention is concerned with plant growth
regulating and weed killing agents. The invention is also
concerned with a process for the manufacture of said agents and
w:Lth a method of reguLating plant growth by means of said agents
or the essential active ingredient thereof.
According to the present invention an agent for the
regulation of plant growth or the killing of weeds contains an
effective amount of 6-amino-_-toluic acid in association with a
compatible carrier material. These agents are particularly useful
as post-emergence and pre-emergence plant growth regulators and
herbicides. However, the post-emergence plant growth regulating
activity is predominant.
Further according to the present invention a method for
the regulation of the growth of intact plants or the killing of weeds
comprises treating the intact plants to be regulated or the weeds
to be killed with an effective amount of 6-amino-o-toluic acid or a
plant growth regulating agent or weed killing agent as specified
above. The method preferably comprises effecting said treatment with
a read-y-to-use formulation containing 0.0001 to 15%, more preferably
0.01 to 10%, even more preferably 0.1 to 5%, particularly 0~1 to 2%,
more parcicularly 0.1 to 1% and most particularly 0.1 to 0.5%g by weight,
of 6-amino-o-toluic acid. Preferably the ready-to-use formulation is
in the form of a solution, suspension or emulsion, or alternatively
in the form of a dusting powder, granules or micro-granules.
The ex~ression "plant growch regulator" as used in this
specification denotes, for example, a compound which either retards
~ - 2 -
.~ . ~
', :. .. .' ., .:, : ~
~Q~ 23
or stimulates the growth of main or side branches or shoots of
pl.ants. Such a compound is capable of influencing the flower
:Lnitlat:lon c~nd fo~nation, the shoot or branch
- 2a -
; ~ : , , . . . -
:: . ; : , :
7~L4;~3
~o~mation, the parthenocarpy, the abscission o~ fruit and/or
leaves and the ripenlng o~ ~it and/or leaves wi-th or withou-t
the prior application of fertilisers. In addition, euch com-
pounds have an e~`fect and an influence on the transport o~
subs-tances wi-thin the plants; for example, a stimulation of the
late~ ~low and/or the me+abolism or, ~or exc~mple, an increase
in the sugar content withln the plantl which may also increa;e
~rost resistance. Such a compound may a~fect the ~xtent o~ sto-
m~tal opening, thu~ Increasing drought resistance and reducin~
or even eliminatlng the hsrl~fuL effects of at;mos~!leric
pollutan-ts (e g. ozone and sulphur dioxide). 6-Amino-o-toluic
acid is especially active in stimulating latex flow.
The expression "intact plant" deno-tes a normal growing
plant as oppo~qed -to a detached part of a plantj e.g., stem
~egments~ coleoptiles or any other explant.
In shrubs, for example, this regulating activity
produces a retardation of the growth in height with concomitant
stimulation of the side-growth.
~ he plant growth regulating agents provided by the
present invention are especially active in regulating the
growth of -the following plants (especially young plants):
. . . . .
~, . ~: . . , :
:'. : ' ..
~,
a) Cereals such as corn, rice, wheat9 rye, barley9
oats etc;
b) ~rees and shrubs such as frui-t trees (e.g. apple,
pear, peach, cherry and lemon) as well as cocoa, tea9 coffee,
banana~ rubber, olive and walnut~
c) Ornamental plants such as privet, hornbeam, whi-te
cedar, juniper, rose9 azalea, chrysanthemum, poinsettia,
cyclamen, pyrocantha9 forsythia, magnolia, petunia and
bromeliad;
d) Field plants such as sugar cane, grapevine, cotton,
soya bean, groundnut, tobacco, flax, sugar bee-t and pineapple9
e) Vegetables such as Solanaceae (e.g. tomatoes),
legumes, pumpkins, melons etc;
f) Berries such as strawberries, bilberries9 raspberries,
5 blueberries, blackberries 9 and redcurrants; and
g) Grasses.
According to the process pro~ided by the present
invention the plant growth regulating and weed killing agents
aforesaid are manufactured by mixing an effecti~e amount of 6-
amino-o-toluic acid with a cqmpa-tible carrier material~
In order to achieve a homogeneous distribution of 6-
amino-o~toluic acid in the presen-t plant growth regulating
and weed killing agents9 it is mixed with conventional liquid
or solid adjuvants~ modifiers~ diluents or conditioning agents
: ~ ~ ..................... ..
,.. ...
whieh are customary in plant growth regulating and weed killing
agents and the resulting mixture is formulated into solutions,
emulslons, emulsifiable eoneentrates, dispersions, dusts,
granulates or wettable powders.
Plant growth regulating and weed killing agents in the
form of liquid formulations suitable for direet spraying ean be
prepared, for example, in the form of aqueous solutions -
whenever possible - or as solutions in solvent mixtures, for
example acetone and water.
Emulsifiable eoneentrates containing 5 - 50% or more, by
weight, of 6-amino-o-toluie aeid depending on the solubility thereof
ean be prepared using suitable solvents sueh as N-methyl-pyrroli-
dine, dimethylform~mide, eyelohexanone ete. Surfaee-aetive
substanees (e.g., wetting agents, dispersants, emulsifiers
ete) are added in a sufficient amount to produce a formulation
having the desired characteristics.
Typical forms in which the plant growth regulating agent
of the invention may be put up are (a) concentrates, e.g. aqueous,
eontaining from 10 to 659 by weight, of the active eompound, (b)
ready-to-use solutions eontaining 0.0001 to 10.0%, by weight,
of aetive eom~ound; (c) water-soluble powders containing from
10 to 90%, by weight, of active compoundl (d) sprayable powders
containing from 35 to 65%, by weight, of active compound, (e)
dusting powders or granules eontaining 2 to 10%, by weight, of
.. , :
,,, ,, . . ~ ,
active compound; (~) ~`lo~lable l:i~uids containing lO to 40~, by
weight, of active compound.
The vari.ous application ~orm~ can be better adapted to the
varlous purposes -for which 6-amino-o-toluic acid may be used
if ~ub~tances which improve the di~persion, adheslon, pene-
tration and resistance to r~in are a~ded, Such sub,stances
lnclude fatty aci.d~, wa~e;l~ re~i.ns, wetti.ng e{~nt~,
emulsifiers, mincral oils, vegetable oils 9 binding agents etc~
In a similar manner, the biologicalspectrum of the present plant
growth regulating agents may be greatly broadened by the
addition of subs-tances having bactericidal, herbicidal or
fungicidal properties or by the addition of fertilisers,
chelate-formin~ agents and o-ther plant growth re~ulators.
Examples of herbicides and plant ~rowth ~egulator~
which can be present in the plant gro~'.h regula-ting agent~
provided by the present invention are:
2~2-dichloropropionic acid 9
N-(4-aminobenzenesulphonyl)methylcarbamate~
2 chloro-4-ethylamino-6-isopropylamino-1 9 3,5-triazine,
- L~chloro-2-oxobenzo-thiazolin-3-~l-acetic acid,
5-bromo~6-methyl-3-~l-methyl-n~propyl)uracil 9
3,5-dibromo-4-hydroxybenzonitrile~
D,N-ethyl-2-(phenylcarbamoylo~y) propionamide 9
', ': ,,:, : :.
! ~ ~
; , ~
:~ `
L23
-- 7 --
N-(4--bromo-3-chlorophenyl)-N'-methoxy-N'-methylureA,
methyl 2-chloro-9-hydroxyfluorene-9-carboxylate,
N'-4-(4~chloropheno~)-phenyl-N,N-dimethylur~&,
isopropyl-N (3-chlorophenyl)-carbamato,
2,3,5,6-tetrachloroterephthalic acid dimethyl ester
(~CPA)~
2,4-dichlorophenox~acetic acid
4-i~opropylamino-6-methylamino-2-methylthio-1,3 9 ~-
~triazine,
n-butyl 9-hydroxyfluorenç-9-carbox~late,
ethylene, . .
naphtho~yacetic acid,
3,6-dichloro-2-metho.cybenzoic acid,
(+)-2-(2,4-dichlorophenoxy)propionic acid,
9 910-dihydro-8a~10a-~iazoniaphenanthrene-2
N'-(3~4-dichlorophenyl)-N~N-dimethylurea,
gibberellic acid,
.indolylacetic acid,
indolylbutyric acid~
4-hydroxy-3,5-diiodobenzonitrile-,
; N'-(3,4-dichlorophenyl)-N met~.oxy-N-methylurea~
(4-chloro~2 methylphenoxy)acetic acid,
4-(4-chloro 2-methylphenoxy)bl-tyric acid9
~ 2-(~-chloro-2-methylphenoxy)propiGnic acid,
N-(benzothiazol-2-yl)-N,N'-dimethylurea~
N'-(3-chloro-4-methox~phenyl)-N,N-dimethylurea,
- ::: . - . . .
~ 23
1,2,3~6-tetrahydro-3,6-dioxopyridiazine,
N'--(4-ehlorophenyl)-N-methoxy~ -methylurea,
N'-(4-ehloropheny])-N,N-dimethylurea~
napht~.ylaeetie aeid,
N-1-naphthylphthalalaic aeid,
2 9 4-diehlorophenyl ~nitrophen~l ether,
1,1'-dimeth~1-4,4'-~ipyridylium-2A,
3-(m-tolylearbamoylox~)phenyl earbamate 3
4-amino-3,5,6-triehloropieolinie aeid
4,6-bis-isopropylamino-?-methylthio-1,3,5-triazine,
N-(3~4-dichlorophenyl)-propionamid
isopropyl~-phenylcarbamate,
5-amino-4-ehloro-2-phenylpyridazin-3(2H)-one,
N-dimethylaminosuceinic aeid,
2 chloroethylphosphonie aeid,
tributyl-2,4-diehloroben~l-phosphonium chloride,
2~4,5-triehlorphenoxypropionic acid,
2 7 3 9 6 -triehlorobenzoie aeid;
2-chloro-4,6-bis-ethylamino-1~,5--triazine~
sodium ehloroaeetate,
~4,5-trichlorophenoxyacetic aGid;
5-ehloro-6-meth~1-3-tert.butyluraeil,
4-ethylamino-2-methyl-thio-6-tert.butylamino~1~3,5-
-triazine-(tert.butyryn)~ I
2~3,5-triiodobenzoic aeid and
1~ 1 7 4-trimethyl~6-isopropyl-5~propionyl-indane~
.,
:
.
~7~ 3
Examples of fungicides which may be present in the
plant growth regulating agents provided by the present invention
are:
2,4-dichloro-6-(o-chloraniline)-S-triazine,
2,4,5,6-tetrachloroisophthalic acid nitrile,
p-dimethylaminophenyldiazo sodium sulphonate,
1,4-dichloro-2,5-dimethoxybenzene,
manganese ethylene-bis-dithiocarbamate,
zinc ethylene-bis-dithiocarbamate,
coordination product from zinc and manganese ethylene-
-bis-dithiocarbamate,
methyl l-(butylcarbamoyl)-2-benzimidazole carbamate,
2-(4-thiazole)-benzimidazole and
cis-N-~(trichloromethyl)-thio]-4-cyclohexene-1,2-
-dicarboximide.
According to a further feature of the present invention, a
method for the regulation of plant growth or killing of weeds comprises
treating land in which said plants are growing with 0.1 to 2n kg, more
preferably 0.5 to 10 kg, still more preferably 0.5 to 5 kg, or most
preferably 1 to 3 kg of 6-amino-o-toluic acid per hectare or with an
amount of plant growth regulating or weed killing agent corresponding
thereto.
The amount of 6-amino-o-toluic acid which can be used for
the regulation of plant growth and killing of weeds may be based on the
results set forth hereinafter. However, it will be appreciated that these
res~ts are not exhaustive and that, in addition, numerDus other factors
influence the amount used. ~or example, the amount can vary not only
~/
~ _ g _
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: .:~. :.: :. . .. ~ .
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:L~7~L~;23
between diff`erent species of plants 4ut also ~thin a specific
species (e.g. depending on factors such as the size and the age of
the plant), the time Or year, the type of soil and climatic
conditions at the time of` use such as the air temperature, light
intensity, rain
- 9a -
., ,. i.. . .
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:: . , ,: : .
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-- 10 --
and wi.nd. ~urthermore, if the plant growth regulating and weed
killing agent comes into con-tact with the plant via irriga-tion
o~ -the soil,high.er concen-trations will be necessary since,
with this type of use, the plant is indirectly trea-ted in
comparison with a direct trea-tment by appIication o~ the plant
growth regulating and weed killing age.n-t on to leaves and
stems (e.g. by spraying).
Accordingly, the amount of the plant growth regulating
or weed killing agent varies according to the plants to be
controlled9 the amount required for application, the method of
application and the degree of regulation of plant growth which
is desired. In general, the present agents contain less than 50~o
of 6-amino-o-toluic acid in a ready-for-use spray form, e.gO
35 to 65% in powder form and up to 10~ in liquid form.
In principle~ the amount of 6-amino-o-toluic acid which
is used is chosen so that an effective control of the plant
~rowth is achievedO Accordingly~ the choice of the minimum
amount of 6~amino-o-toluic acid used is governed by the
minimum amount o~ 6-amino~o-toluic acid which is able to ef~ect
the lower limit of growth retardation desiredO The choice of
the ma~imum amount of 6-amino-.o-toluic acid used i~
correspondingly governed by that amount of 6-amono o-toluic
acid which is able to bring abou-t the upper limit of grow~h
retardation desired. In the control of grasses9 particularly
. /0
- , .... ~ -
. . ~ . : .:~
2~ ~
home lawns and industrial turfs, e g. golf courses, it has beenestabllshed -that a maximum grow-th retardation as evidenced by
diminished gra~s height as compared to an untreated control of
abou-t ~0%-60~ iæ desirable with about 50a/o growth retardation
preferred. Any retardation less than 40a~0 is ineffecti~e in
that grass control is not substantial
enough to have a significant aesthetic effect and to reduce or
eliminate manual care. On the other hand, retardation greater
than 60~o results in an undesired skimpy appearance to the lawn
or turf with subsequent invasion thereof by weed~ and other
undesirable plants.
The amount of 6-amino-o-toluic acid corre~ponding to
these criteria or bringing them about i~ determined by the~e
aspects of the -tomato plantO In order to achieve post-emergence
growth regulating and weed killing acti~ity, amounts of O.5 kg
to 10 kg or more of 6-amino~o--toluic acid per hectare ar~ usedO
In a similar manner, the best post-emergence growth regulating
activity is generally obtained using amounts which lie between
1 kg and 5 kg or more of 6-amino-o--toluic acid per hectare. A
preferred range for spray solutions lies between 1 part per
million and 150 000 parts per million or more depending on the
plant species -to be treated. An especially preferrred range lies
between 100 parts per million and 109000 ~ar-ts per million~
A further advantage of plan-t growth regulating agents
-
2;~
- 12 -
containing 6 amino-o-toluic acid lies in the ab~ence o~ both
a laetlng ef~ect on the plants and a residual activity which
remains in the soil, 6-~mino-o-toluic acid decompo~es slowly
and there i~ accordingly a consequent reduction in activity,
This e~fect has advantages since
,
a) a short,-term effec-t which may be lengthened by
subsequent ~urther treatment is produced;
b) the normal growth behaviour of the plant re-occur3
i.n step with the decrease in activity; and
c) no harm~ul residues remain either on the plant
or in the soil.
~he duration of the retardation effect varie~ according
to factors such as the type of plant treated, climatic
condition~ etc~
Although 6-amino-o-toluic acid possesses a plant growth
regulating activity9 it iæ virtually non-togic to ani~als.
There are weed~ which~ when treated as described above, are
killed~ Examples of such weeds are mentioned in E~amples 2 and 7
~ hereinafter~ Purther example3 o~ weed~ which are killed are ~0~.
: 20 Sorghum halepense~ Imperata cylindrica, Panicum spp. and Paspalum spp.
' :
- The following Egample~ illustrate ~ariou~ formulations
of the plant growth regulating and weed killing agent of the
-:; ,j ... . . . :; ,-
. . ., .. .. ~ ,...,..~ , ,;
~ : . . ~ :
LZ3
-- 13 --
invention,
A. Aq~eous formulations.
~ ecause of the amphoteric nature of 6-amino-o-toluic
acid, it is possible to form more or less water-soluble salts
by reaction with bases or acid~.
a) With bases.
A typical formulation is:-
6-Amino-o-toluic acid 200 gms.
Diethanolamine 150 gms.
Deionised water ad 1000 mlsa
Instead of diethanolamine there can be used othe bases,
such as dimethylamine, triethanolamine, aminome-thyl-propanol
and morpholine. The concentration of -the active substance
depends on the solubility of the salt. These ~ormulations
can also contain an amount of sur~actant, in order to impro~e
the wetti~g power, and consequently the activity, of their
ready-~or-use dilute systems. The formulations will normally
be diluted, before use, to an active ingredient concentration
between 0.01 and 1.0% by weight, preferably 0.05 to 0,8% by
weight. Suitable "before dilution" formulations are as
~ollows:-
.
(i) I~1or a 008~ acti~e substance concentration -
6-amino-o-toluic acid ` 200 g.
Sur~actant ~.25 g~
Diethanolamine 150 g.
D~ionised ~ater ad 1000 ml~.
- /3 -
- , .- .
~6~714~3
-- 14 --
, , ,
(ii) For a 0.05~ active subs-tance concentration -
6-amino-o-toluic acid 200 g.
Sur~actant 100 g.
Diethanolamine 150 g.
Deionised w~ter ad 1000 mls.
The sur~actant may be an anionic surfactant, e.g.
an alkali metal salt o~ an al~yl sulphate, such as sodium
lauryl sulphate, or an alkali metal salt of an alkyl
arylsulphonic acidJ such as sodium dodecyl benzenesulphonate;
,
or a non-ionic sur~actant, e.g. condensation produc-ts o~
ethylene o~ide withaLkyl phenols (such as the condensation
product of nonyl-phenol with 8-10 moles ethylene o~ide) a~
with fatty alcohols (such as the condensation product of
stearyl alcohol with 8-10 moles ethylene oxide).
b) With acids.
Salts may be formed by reaction of 6-amino-o-toluic
acid with such acids as hydrochloric, sulphuric, phosphoric
; and acetic acids. ~he salt formed with hydrochloric is the
most soluble and is preferred. Typical formulations may be
prepared ~rom the following batches of ingredients~
(i) 6-amino-o-toluic acid 100 g~ -
HC1 (321o~ 151 g.
Deioni~ed wator ad 1000 ~ls.
(ii) 6-amino-o-toluic acid 100 g.
Sur~actant 6.25 g.
HCl 151 gO
Deionised water .ad lO00 ~ls.
: . . . .~ .,: . .: . .
23
-- 15 --
(thi~ gives, on dilution, a 0.8% active ingredient content),
(iii) 6-ami~o-o-toluic acid lO0 gO
, .. . . .
Surfactant 100 g.
Hal 15 1 g .
Deionised ~aterad 1000 mls.
(this gi~es, on dilution, a 0.05% act.ive ingredient content).
The surfact~nt may be non-ionic, as described above, or
cationic, e.g. alkylbenzylammonium compounds such as
dodecyl~imethylbenzylammonium chloride.
B. Powder-form water-soluble for~ulations (by salt-formationj
~wo typical ~ormulation~, one containing a base and
the other an acid~ are as follows:-
ii
6-amino-o~toluic acid 20.0- 20.0 ~.
Soda, calcined 15.5
Sodium lauryl sulphate (sur~actant) 1.0
~actose 63.5 6Ç~0
Sulphaminic acid 1~.0
: . Ethylene oxide-propyle~le oxida 1.0
solid block polymeri~ate(80~0
polyethyleneglycol ether chai~)
(non-ionic surfac~ant)
~hese formulations are prepared by mixing the ingredient~
and finely mllling them to give a freeflowing powder which
i!~ wettable with water and dissolves to a clear solution.
'' . , - '' ...
.
:
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~7~23
~ 16 -
C. Solid forrnula-tions. ~~ ,
(i) SE~y ~wder (wettable po~.~der)
6-amino-o toluic acid 50.0 g.
Hydrated silicic acid 5.0 g.
Sodium lauryl sulphate (surfactant) 1.O g.
Sodium lignosulphonate (dispersant) 2.0 g.
Eaolin B 24 42.0 g.
The ingredients are well mixed and finely milled to gi~e
a free-flowing po~der which is wettable with water and has
good suspension capability.
a~t.
6-amino-o--toluic acid 5.0 g.
Talc 95.0 g.
The components, on intimate mixing and milling, give a
powder with good dusting capability.
(iii) Gran~late.
.
6-amino-o-toluic acid 5.0 g.
Polyethyleneglycol (PEG 500) 2.0 g.
Ca C03, granulated, 1 mm 93.0 g.
The calcium carbonate granules are uniformly sprayed with
the PE~ and are -then mixed with finely milled 6-amino-o-
- tolulc acid. ~he PE~ acts as an adhesive and bonds the
active substance to the carrier particlesO
: .
.~ .
. .
- 17 -
D, Other ~ormulations.
(i) The following ingredient~ are mi~ed and milled in
a ball mill until the particle si~e o~ the active substance
is within the range 1 to 5 microns.
6-amino-o-toluic acid 250 g.
Sodium salt o~ ~ sulphonated 25 g.
naphthalene-formaldehyde conden- -
sation product (dispersant)
~entoni-te 15 g.
Deionised water ad 1000 ml9.
There i8 obtained a homogeneous, pourable preparation
which is dispersible in water to give a ready-for-uæe spray ;~
dispersion.
(ii) Emulsi~iable concentrate.
6-amino-o-toluic acid 100 g.
Emulsifier 100 g.
Cyclohexanone ad 1000 mls.
(The emulsifier is a mi~ture of a condensation product
.. . . .
obtained ~rom nonyl phenol with 8-10 moles ethylene o~ide
and the calcium salt of dodecylbenzene sulphonic acid). The
active substance and the emulsifier are dissolved in
cyclohexanone to gi~e a clear solution which emulsifies
spontaneously in water and later even solubilises.
(iii) ~}~3~
6-amino-o toluic acid 2.0 g.
Acetone 97.9 g~
Tensio-~ix AS (sur~actant~ 0.1 gO
.
12~
- 18 -
(Tensiofix AS i9 a mi~ture of nonionic alkylphenol deriva~ives,
polyethylene oxide alkylphenol conden~ation product and
anionic dodecyl benzene sulphonate and also contains un-
speci~`ied, but small, amounts of n-butanol r~nd carbon
tetrachloride). The formulation will normally be diluted
immediately before application, to give a concentration o~
active substances of 0.1 to 0.2% by weight, with water
and ~ween 20~
As will be evident from the following further ~xamples,
a particular advantage of the present; invention is that the
plant growth regulating agents possess pre-emergence and
post-emergence plant growth regulating activity when used
for the treatment o~ various plants, the range of plant~
being e~tremely wide. The growth regulating activity of
the present agents will be evident ~rom the following green-
house test for the determination of the post-emergence
- activity.
.. ., . ., ,, ~
' ~ ' ' ~. . ~,
- ~7~23
-- lg --
Example 1
.
Several concentrations of 6-amino-o-toluic acid are
sprayed on to the plant so that a complete spray coating is
obtained. ~he spray solution contains, by weight, 1.0%, 0.5%
or 0.25% of 6-amino-o-toluic acid, 001% of ~ensiofix AS (see
above), 48.9%, 49.4% or 49.65% of acetone and 50% of water.
Three weeks after treatment 9 the plants are assessed for
herbicidal activityO ~he results are given in ~able I.
..
Table I.
-- .
.-- . ... .. .. __ ___ ~
Test plant~ Dosage Dosage Dosage
(kg/hectare) (kg/hectare) (kg/hectare)
.~ 2,5* 5*~ 1~
, . . __ , , ; ..... _ I .
. ~ halepense 80 90 100
Ru~ex obtusi~olius 80 100 100
LE~ 100 100 100
Panioum ~ _ 100 _ _
. ~ .
:(* percentage leaf area necrotic)
_/q _
,.
,
~l~7~3
Example 2
In order to demonstrate growth retarding activit~ in
per cent r01ative to untreated plants on wheat, barley and blue
grass, a solution containing, by weight, 0.4 % o 6-amino-o-
toluic acid, 49.5 % of acetone, 0.1 % of Tensiofix AS and 50 %
of water was used. This concentration of 6-amino-o-toluic acid
corresponds to an amount of 4 kg/he~ctare. The results are given
in Table II.
Table II.
Percentage growth
Test Plants retardation relative
to untreated controls
wheat ~triticum aestivum) 25
~arley (Hordeum distichon) 40
` blue grass (Poa pratensis) 75
Example 3
The growth retarding activity of G-amino-o-toluic
acid, in comparison with that of the known plant growth regulator
2-chloroethyl trimethyl ammonium chloride (CCC), was tested on
wheat (Triticum aestivum "Svenna") and barley (Hordeum distichon
"Union") plants. Solutions (2%) of the active ingredient were
prepared in acetone/water mixtures to which were added 0.2%, by
weigh~, "Tween*" 20 surfactant. The plants were treated in
a greenhouse, at mean relative humidity 70 %, average night
temperature 18C and day temperature 22 - 26 C,
* Trademark
~ 20 -
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.: : . .: .
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1~17~3
- 21 -
with treatment solutions in various amounts. ~he plants were
treated twice, at one of two growth stages, either at the 3-
leaves stage or at the 6-leaves stage 9 and -the average lengths
of the plan-ts (six in each group) were measured in each case
3 weeks after each application, The results are set out in
~able III~
- -
~able III.
. ~ Average length in cm~.
. Te~t plant Plant Untreated¦CCC 6-amino-~ L~ ~id
_ . Stage Oppm __ IOOOppm lOOOEEI 5~ E 250p
~riticum aestivum 3 leaves ~5~9 9.9 5.6 7.2 12.1
._
n l~ 6 ~ 24.0 19.216.2 23.5 25.8
Hordeum distichon ~ " 19.8 16.0 9.2 9.8 18.7
. . __ .
. 6 " 3~.4 26.5l14.3 25.3 29 8
It is seen that at 1000ppm 6-amino-o-toluic acid was æuperior
to CCC on both species and at~both growth stages.
15 E~mple 4
The growth retarding activity of 6-amino-o-toluic acid ~ ;
in comparison with that of the known regulating agent "~ustar"
(3~-(trifluoromethylsulfonamide)- -acetotoluide) was tested
on four grass species listed in ~able IV below. Solutions of
the active ingredients were made up in a manner similar to those
of Egample 3 but with only 0.1% "~ween" 20 sur~actant. The plant~
t ~ ~ Je ~
,'' , ' , . ...
~7~ 23
- 22 -
were treated in a greenhouse, at mean relative humidity 70%,
a~erage night temperature 18~ and day t~mperatùre 22-26C,
at variou~ treatment levels ~rhen the plants were 4 cms in
height. Their heights were again measured 3 weeks later
and the average height of 6 plants in each case is recorded
in ~able IV, together with the percentage growth reduction rela~e
to untreated plants.
Table IV.
. ~
.. ` ~ . _ _ - ~
~ength o~ plant in cms.
Test plant - _ _ _ _
Untreated ''Su~ ,tar'' 6-amin, )-o-toluicacid¦
Eg.active ingredient/ha O 4 2 1 O.5
Poa pratensis 25 14 18 5 5 5
~olium perenne 28 20 26 21 26 27
:~ A~rostis tenuis 21 6 7 5 9 13
~estuca rubra 20 10 16 5 5
_ _ _. . _
Growth reduction in ~0 relative to
untreate~
Poa ~ O 44 28 80 80 80
olium ~erenne 0 29 7 25 7 4
A~rostis tenuis 0 71 67 76 57 38
Featuoa.r bra 0 50 20 75 75 45 L
It is seen that 6-amino-o-tolu~c acid at 1kg/ha is superior
to "Sustar" at 2kg/ha on all ~our specie~.
- 2 ~ -
~, . . . . ..
t ' ' ' ' '"" '' "'. ."' ' ' '
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, '":
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~ 3
- 23
Example 5
'~he ~.rthenocarpic activity of 6-amino~o-toluic acid
was tested, in comparison with the known gibberellic acid
~GA3) on She tomato species ~ a~ esculentum "Ti~y Tim
under the same greenhouse conditions as described in ~xample~
and 4. The application solutions were acetone/water soluti.oi1s
.. . . . . . . . . .
containi.ng 2~ active ingredient and 0.2~o "Tween" 200 l~1hen
the tomato plants showed flowers and green ~ruits 10 flower
buds per plant were emasculated and 2 drops o~ test solution
were applied to each bud using a micropipette. When the
fruits matured, 59 days later, the~ were counted, opened
and checked for æeeds. The results are given in ~able ~.
Ta~le V.
~ ,
Number o~ full~ dev.~loped fruit~
GA3 (ppm a.iD) 6-amino-o-toluic acid (pmm. a.i.~
50 10 1000 100 1¢~ ¦ 1 o
~ ~ _ ~ . ......................... I _ .
0 0 8 9 7 10 0
. .. __ ___
It ~ll be seen that only those plants treated with 6-amino-
o-toluic acid set ~ruit. Further, it was noted that all o~
these ~ruits were parthenocarpic.(seedless).
-- ~3--
'
', :
LZ3~
- 24 -
Example 6
~ oma~o ("Tin~ Tim") plants were ~prayed to run o~-
~with a 100 ppm solution o~ 6-amino-o-toluic acid when hal~
tn~ ~ruits on the ~irst truss were red. Ripe ~uits were
picked over the next 19 days. At the end of this period
~7.2% o~ all fruits had ripened on the treated plants against
22.9~ on the controls. Since ripening is associated with
~p~ene it is logical to assume that other ethylene e~fects
e.g. latex stimulation, ~ruit abscission, de~oliation o~
cotton and nursery stock plants, are achieved through use o~
this compound.
- Example 7
:` :
~ he post-emergence herbicidal activity o~ 6-amino-o-
toluic acid was demonstrated by spraying ~a~a~a~ ~3a~
(3 1ea~ed stage) and Rume~ obtusifoliu~ (2 leaved stage) at
.. . . . .. . . .
3 kg a i.Jha using a spra~ volume o~ 1000 I/ha. ~hen
the plants were assessed 3 weeks later a 70% and 100~o
kill was observed on D~ L3~ and R ~33
respectively.
.
, . .
.. .. . ... . .
.:: .. ~.. .
, , ,~ ' '
23
-- 25 --
~ he 6-amino-o-toluic acid may be marketed in portion~ o~ ;
varying size in packages or containers suitable for agro-
chemical purpose~ These packQges or containers may consist of
paper9 pla~tic material, glass or metal. The 6-amino-o-toluic
acid in the~e package~ or container3 may be used for the
regulation o~ the growth of plants or for the killing of weeds.
In a preferred embodiment the plant growth regulating and
weed killing agent contains an eff~cti~e amount of 6-amino-o-
toluic acid in association with at least one competible carrier
material of a molecular weight of 200 or more.
We are aware that the literature has reported an
attempt to determine whether 6-amino-o-toluic acid has
any plant growth-regulating activity. Such attempt con-
cluded, in contrast to our ~indings, that this compound
was inactive, i.e. it had no plant-growth regulating
activit'.
~ :. ::: .,,.: .. ::
