Note: Descriptions are shown in the official language in which they were submitted.
~s~
METHOD FOR DWARFIN~ THE STEM OF SUNF~OWERS
SUMMARY OF THE INVENTION
The present invention relates to methods for
dwarfing and~or stiffening the stems of sunflowers by apply-
ing to said plants or to ~he soil in which said plants seeds
are sown, a growth regulating amount of a compound repre-
sented by formula (Ia) or (Ib):
~ X m or ~ R35~1m ~-m
Ia Ib
whcrein Rl and R2 each are Cl-C3 alkyl or phenyl; R4 is
hydrogen~ OH~ Cl-C18 alkyl, Cl-C3 haloalkyl, Cl-C4 alksxy,
C2-C4 alkenyl, C2-C~ haloalkenyl, C2-C4 alkynyl, ~ CH2-,
~ CH2 ,_4~OOCH3, -CH2COOC2Hs, -OP(O)(OC2Hs)2, halogen,
nitro or R7 ~ ; R7 and R8 each are hydrogen, halogen or
nitro; R3 and Rs each are Cl-C12 alkyl, Cl-C~ alkoxy, C3-C6
cycloalkyl,~ C3-C6 cycloalkylthio, halogen, NH2-, (CH3)2N-,
C6H~NH, C6HsO-, C6H5S-~ ~ ~3 ~ ~ ~ N~N-~ O~_~N-~
C ~ ~ ~ ~ -CH3-N N-, or ~ ~ ~ U, V and W each
CH3 COOC2Hs ~
are hydrogen, halogen, Cl-C4 alkyl, Cl-C3 alkoxy, CN, N02,
CF3, CH3S, CH35Q2, CH3 CONH, CH300C, CSH5 or C&H50; R6 is
1~51B9O
--2--
(H)n or (CH3)n; n is an interger of 0 or l; the symbol
---- used in the above structures represents a single or
double bond; m is an integer of l, 2 or 3; X is acetate,
sulfate, hydroxide, hydrogen sulfate, methyl sulfate, ben-
zene sulfonate, (Cl-C~) alkylbenzene sulfonate, (Cl-C4)
alkoxybenzene sulfonate, nitrate, phosphate, hydrogen,
phosphate, dihydrogen phosphate, carbonate, ~Cl-Cl2) alkane-
sulfona~e, bromide9 chloride or iodide.
A preferred group of compounds of formula (Ib)
may be illustrated by formula (II3 below:
l~ / 2
R4 ~ ~ m
wherein Rl to Rs, m and X are as hereinabove defined; R6
is hydrogen or methyl.
Another, more preferred group of compounds of
formula (Ia) may be illustrated by formula (III) below:
Rl
~ 4 3 Im
wherein Rl to Rs, m and X are as hereinabove defined.
The most preferred group of compounds of form-
ula (Ia) may be illustrated by formula (IV) below:
~4 1 X m
~5 ~
--3--
wherein Rl to R5, m and X are as hereinabove defined.
Among the compounds illustrated and represented by
~ormulae II, III and I~7above and of primary interest are ~hose
wherein Rl and R2 are each methyl or phenyl; R3 and Rs each are
5 Cl, Cl-C2 alkyl, ~ S , ~ O- ~ ~ or V
U is hydrogen, V and W each are hydrogen, Br, Cl, F, CH3,
CH30, CF3 or CN; R4 is hydrogen, CH3, C2H5~ CH2-CH-CH2-~
CH-C-CH2-~ ~ CH2-, CH30, (CH3)2CH-O-, N02 or Cl; X
10 is OH, Br, I, sulfate, hydrogen sulfate, methyl sulfate, ~-
toluene sulfonate, dodecyl sulfate or nitrate; m is 1 or 2;
X is acetate, methyl sulfate, benzene sulfonate or ~-toluene
sulfonate.
OE specific interest is the compound: 1,2-dimethyl-
15 3,5-diphenylpyrazolium methyl sulfate.
As indicated above, application of growth regulat-
ing amounts of formula (Ia) and ~Ib) compounds to sunflowers,
and other agronomic crops or to soil in which the seeds of
said plants are sown produces a dwarfing effect in said
~0 plants while increasing the stem stiffness thereof.
Dwarfing and/or stiffening of the stems of sun-
flowers is most advantageous to the farmer as it tends to
minimize the lodging of these plants; since lodging usually
results in reduced yield of the affected crops.
Lodging, in the present application, refers to the
deflection of the plant from the vertical, varying in degree
from only a slight deflection to complete deflection ~i.e.
plant prone) caused by, in most cases, the action of wind
and/or rain on the plantsO This deflection is such that when
30 the causal agent (windg rain) is no longer present, tbe
defiection is neither immediately nor completely overcome.
Moreover, where extensive or severe lodging has occurred~ the
crop may be difficult to harvest and the yield markedly
re~uced.
An additional advantage of dwarfing may be more
uniform flowering: the formation of an increased number of
capitulums ~wherein the term: "capitulum" is used to describe
~ ~s~
--4--
the area of receptacle or flower head no~ including ray
flowers), and earlier and more uniform maturing of plants.
Early and uniform matur;ng allows the early harvesting of
crops, and in the case of sunflowers will reduce losses due to
5 bird feeding.
Dwarfed plants, especially sùnflowe~s, may also be
easier to treat with insecticides and fungicides and allow
better control of head feeding insects and fungi. Such plants
appear to be more resistant to, or are more easily treated for
10 Phoma black stem disease.
In practice we have found that application to the
foliage of seedling plants of from about 0.06 to 0.5 kg/ha and
preferably about 0.125 to 0.50 kg/ha is to achieve the de-
sirable and advantageous biological responses in plants des-
15 crib~d above.
Surprisingly, it has also been found that the form-
ula Ia or Ib comounds of this invention are effective for
reducing the relative stem growth of broadleaf plants and for
increasing the stem stiffness thereof, particularly for
20 broadleaf agronomic crops such as sunflowers, when said com-
pounds are applied preemergence to soil in which seeds of said
plants have been sown. When used in this manner said formula
Ia or Ib compounds are generally applied at rates of from 0.16
to 0.50 and preferably 0.125 to 0.50 kg/ha.
The salts of formula Ia or Ib usually are quite
soluble in wa~er and are con~eniently formulated for foliarapplication as compositions of soluble powders, aqueous con-
centrates or emulsion concentrates, which are usually dis-
persed and/or dissolved in water or in other, inexpensive,
30 liquid diluents for application to the foliage of said plants
as a liquid spray.
A typical soluble powder can be prepared by grinding
together approximately 46% by wei~ht of a finely divided water
soluble, inert carrier such as urea, 50% by weight of the
35 pyrazolium, pyrazolinium or pyrazolidinium salt, 3% by weight
of the sodium salt of condensed naphthalene sulfonic acids and
1~ by weight of sodium N-methyl-N-oleoytaurate.
~Ls ~
--5--
Emulsion concentrates and aqueous concentrates may
be prepared by dissolving 15% ~o 70% by weigbt of the formula
Ia or Ib compound in ~5% to 30% of a solvent such as water,
N-methylpyrrolidone~ lower alcohols, methylisobutylketone,
5 2-methoxy ethanol, propylene glycol,diethyl glycol, diethyl-
ene glycol monomethyl eth~r, formamide, methylformamide,
and the like, and mixtures thereof. Advantageously, surfact-
ants such as polyoxyethylated vegetable oil or an alkyl
phenoxy polyoxyethylene ethanol are also incorporated in
10 amounts of 1% to 5% by weight of said concentrate.
The invention is further illustrated by the ex-
amples set forth below which are not intended to be limiting
on the invention.
Example 1
15 Evaluation of 1,2-dimethyl-3,5-diphenylpyrazol;um methyl sul-
fate as dwarfing a~ent for sunflowers
In the following tests, the test compound is dis
solved in water at the final concentration corresponding to
the kg/ha rates indicated in the tables below. The solu~ion
20 also contains 0.25% v/v colloidal BIOFILM~ (product of
Colloidal Products Corp.) which is a mixture of alkyl aryl
polyethoxyethanol, free and combined fatty acids, glycol
ethers, dialkyl benzene carboxylate and 2-propanol.
The plant species used in these tests is sun-
25 flowers, Herlianthus annuus DO 164 variety. The plants aresprayed at the two true leaf (fully expanded) stage at rates
of 0.25, 0.125 and 0.0625 kg/ha of test compound.
The plants are held for 64 days aEter treatment
30 when they are measured and harvested. All treatments are
; replicated six tîmes and comparisons made against untreated
- controls. Data obtained are reported in Table Ia below~
~eL~eo~ as percent reduction in plant height over untreated
controls.
~ ~ s~
Table Ia
Evaluation of test compound
Dwarfing of Sunflowers
% Reduction in plant
5 Rate: k~/haheight over untreated con~rols
.
0.25 66.2
0.125 37.2
0.0625 27.~
In this Example the weight of the plants and of
10 flowers is also determined. The results are given in Table
Ib below as % increase (+) or decrease (-) in weigh~ over
untreated controls.
Table Ib
Evaluation of the effect of the test compound on
the weight of plants and flowers
% weight ~/O weight
Rate change of change of
kg/ha plants flowers
0.25 + 17.8 - 14.8
0.125 - 1 - 18.3
0.0625 + 18 + 7
Example 2
Evaluation of 1,2-dimethyl-3,5-diphenylpyrazolium
methyl sulfate a~ agent for sunflowers
In the followin~ tests, the test compound is dis-
solved in water at the final concentration eorresponding to
the kg/ha rates indicated in the Table below. The solution
also contains 0.25% v/v Colloidal BIOFILM~ ta product of
Colloid~l Products Corp.) which is a mixture of alkyl aryl
30 polyethoxyethanol, free and combined fatty acids, glycol
ethers 7 dialkylbenzene carboxylate and 2-propanol.
The plant species used in these tests is sunflower,
Helianthus annuus DO 164 variety.
The solution of the ~ompound under test is sprayed
35 at a rate of 7471~ha with a moving nozzle along an overhead
stationary track. rhe spray nozzle moves at a constant speed
1~53~8~(~
--7--
over the plants.
The plants are grown in plastic pots, and are well
established at the time of treatment. The seedlings of sun-
flowers, are at the 6th lea~ stage. Plants are watered prior
5 to treatment and then sprayed to provide the kg/ha rate of
test compound desired. After spraying the plants are placed
on greenhouse benches and watered and fertilized in accord-
ance with normal greenhouse procedures.
All treatments are replicated f ive times and com- -
10 parisons made against untreated controls at 10, 21 and 40 days
(harvest) post-treatment. The weight of plants and flowers
is also determined at the time of harvest. Data obtained are
reported in Table II below as percent reduc~ion in plant
height and percent weight increase (+) or decrease (-) of
15 plants and flowers over untreated controls.
Table II
Evaluation of test compound for
Dwarfing of Sunflowers
Days Post-treatment
1021 40 (Harvest)
% % %
Rate Plant Ht Plant Ht Plant H~
kg!ha reductisn reduction reduction % Plant % Flower
0.5 28.3 57.1 49.8 + 20.8 - 18.5
0.25 13.5 20.9 13 + 16.6 ~ 2.6
0.125 8.8 8.1 1.4 + 4.9 - 5.6
Exa~ple 3
Evaluation of 1,2-dimethyl-3,5-diphenylpyrazolium methyl
sulfate as Dwarfing agent for different varieties of Sun-
flowers
By the methods of Examples 1 and 2, the title
compound is evaluatPd as a dwarfing agen~ on sunflowers,
elian~hus annuus D0 843~ D0 704 and D0 844 varieties.
Da~a obtained are reportred in Table III below as
35 percent reduction iD plant height over untreated controls.
~15~
--8--
Table III
Evaluation of test compound for
Dwarfing of Sunflowers
% Reduction in plant
Rate height over untreated
Variety K ~ controls
0.25 69.6
DO 843 0.125 50.6
~.63 23.2
0.25 63.
DO 704 0.125 34.7
~.063 23.9
0.25 75.0
D~ 844 0.125 27.1
0.063 32.0
Example 4
Evaluation of 1,2-dimethyl-3?5-diphenylpyrazolium methyl
sulfate as a preemergence Dwarfin~ agent for_sunflowers
The pre-emeergence activity of the title compound
is demonstrated by the following ~ests wherein the test
20 compound is dissolved in water at the final concentratiuon
corresponding to the kg/ha rates indicated in Table IV below.
The solution also contains 0.25% v/v Colloidal BlOFILM~ (a
product of Colloidal Products Corp.) which is a mixture of
alkyl aryl polyethoxyethanol, free and combined fatty acids,
glycol ethers J dialkylbenzene carboxylate and ?-propanol,
The plant species used in these tests is sun-
flowers, Helianthus annuus DO 164 variety.
On the day of treatment, 100 ml soil is-put in
plastic pots as base, then the seeds are placed on it and
covered with 50 ml soil. The pots are then tamped to level
30 the soil and the soil is prewetted with water prior to
application of test solution to assure uniform ~preading of
same over the surface of the po~.
The solution of the compound under test is sprayed
a~ a rate of 747 l/ha with a moving nozzle along an overhead
stationary track. The spray nozzle moves a~ a constant speed
over the pots.
After spraying, the pots are placed on greenhouse
benches and wa~ered and fertilized, and the emerging plants
cared for in accordance with normal greenhouse procedures.
All treatments are replicated six times and com-
5 parisons made against untrPated controls at 19 days post~treatment. Data obtained are reported in Table V as percent
reduction in plant height over untreated controls.
Table IV
Evaluation of test compound for Dwarfing
Sunflowers, when applied to soil in
which the seeds of said plants are sown
% Reduction o Plants
Rate Height over untreated
g~/ha controls
0.50 34.6
0.25
0.125 18.7
Example 5
Evaluation of compounds of the invention as dwarfing agents
for sunflowers.
By the metbod of Example 1 and 2, a number of com-
pounds are evaluated as dwarfing agents at the kg/ha rates
indicated in Tables Va, Vb and Vc, respectively.
The plant species used in these tests is sun-
25 flowers, Helianthus annuus D0 164 variety~ The plants aresprayed at the 4 to 6 true leaf (fully expanded) stage at
the rates indicated. The plants are held for two to three
weeks post-treatment when the~ are measured and harvested.
All treatments are replicated six ~imes and comparisons
30 are made against untreated controls. Data obtained are
averaged and reported in Tables Va, Vb and Vc as percent
changes in plan~ beight, number of leaves and of fresh
weight of pl nt over untreated controls, wherein the sym-
bol: ~ represents an increase, and the symbol: - represents
a decrease.
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-19-
EXAMPLE 6
Evaluation of the plant growth regulating effect
of 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate on
sunflowers.
By the method of Examples 1 and 2, the title
compound is applied to sun~lawe~s at the rates indicated
in Table VI, when the plants are at the 4 leaf stage.
Height reduction is determined 12 and 40 days post-~reat-
ment. The number of developed heads are counted at 56
days and yields are determined 98 days post-treatment,
respectively. The data obtained are averaged and compared
to untreated controls. The data are reported in Table VI
below.
TABLE_VI
Evaluation of the dwarfing effect of 1,2-
dimethyl-3,5-diphenylpyrazolium methyl sulfate on sun-
flowers.
DaYs Post-~reatment _ Yield
Percent height No. of developed in ~ in %*
20 Rate reduction heads
kg/ha 1~ 40 16 ~ 98 98
. _ ~ . . ~ ~ .
Control _ 0.0 734.7 _
. . . .. .
0.50 10.0 23.3 11.7 628.085.5
. . . _ . .
0.25 3.3 13.3 0.0 801.0~09.0
. .. __~ . . . ,
0.l25 o.o 6.7 _ 735.7 loo.
0.062 ~.o o.o o.o 798.0 1 lo~. 6
_
= vs the control (100%)
EXA~LE 7
Evaluation of the effect of 1,2-dimethyl-3,5-
diphenylpyrazolium methyl sulfate on the developmen~ and
number o~ eapitulums of sunflowers.
s~
-20-
~. . . IT
~1 f~l 8 1~ tq . . ~O ~
.~; ~'~0 ~D ~ + +
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N Z
~ J-
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--- - --------~ ~
~lS~
-21-
By the method of Examples 1 and 2, sunflowers
(Helianthus annuus) are treated with 1,2-dimethyl-3,5-
diphenylpyrazolium methyl sulfate at the rates indicated
in Table VII below. All treatments:are replicated three
times and comparisons made agsinst untreated controls
using 2 x 10 meter.test plots.
At ths beginning of flowering plant heights are
measured and the number of flowering capitulums plot is
determined.
Sixty days later, at harvest, the number of
capitulums per one 10 meter row is determined. The data
thus obtained are averaged and reported in Table VII
below from wherein it can be seen that the title compound
increases the number of capitulums of sunflowers, when
applied at the 0.25 to 0.50 kg/ha rate.
In the above tests, the term "capitulums" is
used to describe the area of recep~acle or flower head
not including rayflowers.
