CA1151890A - Method for dwarfing the stem of sunflowers and cotton - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE

There is provided a method for dwarfing and/or stiffening the stems of sunflowers, comprising: applying to said plants or to the soil in which the seeds of said plants are sown certain salts of substituted pyrazolium, pyrazolinium and pyrazolidinium compounds, in amounts sufficient to achieve the desired degree of dwarfing and/or stem shortening.

Description

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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

(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 ~

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~

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.

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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.

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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~(~

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~

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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l5~

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~

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~lS~

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.

Claims (9)

28,170 We Claim:

1. A method for dwarfing and stiffening the stems of sunflowers comprising: applying to said plants or to the soil in which the seeds of said plants are sown a growth regulating amount of a compound of formula:

.X-m or .X-m Ia Ib wherein R1 and R2 each are C1-C3 alkyl or phenyl; R4 is hydrogen, OH, C1-C18 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, , , - COOCH3, - CH2COOC2H5, - OP(O) (OC2H5)2, halogen, nitro or ; R7 and R8 each are hydrogen, halogen or nitro; R3 and R5 each are C1-C12 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkyl-thio, halogen, NH2-, (CH3)2N-, C6H5NH-, C6H5O-, C6H5S-, , , , , , , , , or , U, V and W each are hydrogen, halogen, C1-C4 alkyl, C1-C3 alkoxy, CN, NO2, CF3, CH3S, CH3SO2, CH3CONH, CH3OOC, C6H5 or C6H5O; R6 is (H)n or (CH3)n ; n is an integer of 0 or 1; the symbols ----represent single or double bonds; m is an integer of 1, 2 or 3; X
is acetate, sulfate, hydroxide, hydrogen sulfate, methyl sulfate, benzene sulfonate, (C1-C4) alkylbenzene sulfonate, (C1-C4) alkoxy-benzene sulfonate, nitrate, phosphate, hydrogen phosphate, dihydrogen phosphate, carbonate, (C1-C12) alkanesulfonate, bromide, chloride or iodide.

2. A method according to Claim 1, wherein the compounds are of formula:

.X-m and R1 to R6; X and m are as defined in Claim 1.

3. A method according to Claim 1, wherein the compounds are of formula:

.X-m and R1 to R5; X and m are as defined in Claim 1.

4. A method according to Claim 1, wherein the compounds are of formula:

.X-m and R1 to R5; X and m are as defined in Claim 1.

5. A method according to Claim 4, wherein R1 and R2 each are methyl or phenyl: R3 and R5 each are C1, C1-C2 alkyl, , , , or , V and W each are hydrogen, Br, Cl, F, CH3, CH3O, CF3 or CN; R4 is hydrogen, CH3, C2H5, CH2=CH-CH2-, CH?C-CH2-, , CH3O, (CH3)2CH-O-, NO2 or Cl;
X is OH, Br, I, sulfate, hydrogen sulfate, methyl sulfate, 0-toluene sulfonate, dodecyl sulfate or nitrate, m is 1 or 2.

6. A method according to Claim l, wherein the compound is applied at the rate of 0.06 kg per hectare to 0.5 kg per hectare.

7. A method according to Claim 1, wherein the compound is 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate.

8. A method according to Claim 4, wherein the compound is applied to the plants at the rate of 0.12 kg to 0.50 kg per hectare.

9. A method according to Claim 4, wherein the compound is applied to the soil, in which the seeds of said plants are sown, at the rate of 0.06 kg to 0.50 kg per hectare.