Plant growth regulating formulations

Details Plant growth regulating formulations Plant growth regulating formulations

2001-01-02

2002-10-01

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S140000, C504S297000

Reexamination Certificate

active

06458746

ABSTRACT:

The present invention relates to plant growth regulating preparations comprising
a) 0.1 to 20% by weight of a 16,17-dihydro gibberrelin of general formulae Ia or Ib
b) up to 99.9% by weight of an formulation additive selected from the group consisting of
b1) the reaction products of triglycerides based on carboxylic acids having 2 to 30 carbon atoms and ethylene oxide and/or propylene oxide in the presence of a base, and/or
b2) fatty acid esters of sugar alcohol polyethoxylates
c) up to 50% by weight of an organic solvent
d) 0.1 to 50% by weight of a formulation auxiliary different from b1 and b2,
e) up to 50% by weight of additional plant growth regulating compounds.
Furthermore, the present invention relates to the use of the said preparations for the regulation of plant growth.
Numerous plant growth substances are known. Part of these substances are used in agriculture and horticulture in order to induce desired effects, for instance on
seed germination and seedling growth
rooting
dormancy
juvenility, maturity and senescence
flowering
abscission of leaves, flowers and fruits
fruit set and development
tuber formation
growth of shoot and root
photoassimilation
control of unwanted plants
senescence of whole plants or single organs
[cf. R. N. Arteca (1996) Plant Growth Substances, Chapman & Hall, New York.]
Gibberellins (GAs) represent one group of plant growth substances. GAs occur naturally in higher plants where they function as phytohormones being involved in the regulation of growth and flowering and numerous other developmental processes. Certain GAs, particularly gibberellic acid or GA
3
(ent-3&agr;,10,13-trihydroxy-20-norgiberrell-1,16-diene-7,19-dioic acid 19,10-lactone), are commercially available as fermentation products of the fungus
Gibberella fujikuroi.
C-16,17-dihydro GAs and related structures have been known since many years. They either occur naturally in higher plants (e.g. GA
82
and and GA
83
) or in the fungi
Gibberella fujikuroi
(e.g. GA
2
, GA
10
, GA
42
) and Phaeospheria sp. (e.g. GA
82
).
WO 93/03616 and PCT/AU95/000528 describe for the first time the biological activity of known and newly synthesized 16,17-dihydro GAs and their potential utility for agricultural, horticultural and plant breeding applications. In particular the following biological effects have been described as features of the 16,17-dihydro GAs and/or other ring D-modified GAs:
dwarfing
growth retardation of stem and shoot and/or root
promotion of bud break
flowering
improved fruit quality
inhibition of fruit ripening
prevention of whole plant and/or organ senescence
improved fruit set
control of weed growth
inducing male sterility
retarded bud break
tillering
Further details on chemical and biological aspects of distinct 16,17-dihydro or other ring D-modified GAs have been published in the recent scientific literature.
A major obstacle to introduce the ring D-modified gibberellin derivatives described in WO 93/03616 and PCT/AU95/00528 into agricultural and horticultural practice is caused by the costs required to produce these compounds. The production costs are primarily affected by the price of the starting material GA
3
[cf. W. Rademacher (1997): Gibberellins, in Fungal Biotechnology, T. Anke (ed.), Chapman & Hall, Weinheim, pp. 193-205].
There thus exists a need in formulations based oh ring modified D-gibberelin derivatives having improved biologicasl activity and thus better economical feasibility.
The object of the present invention was to provide plant growth regulating preparations based on ring D-modified gibberellin derivatives having a very good biological activity, in particular at low application rates.
This object has been achieved with the plant growth regulating formulations as defined in claim
1
and hereinbefore.
Preferred embodiments of the instant invention are set forth in the dependent claims and the following detailed specification.
The C-16,17-dihydro gibberellins (component a) have the chemical formulae Ia or Ib
wherein A, B, C, D, E and F independently represent hydrogen atoms or hydroxyl groups and the dotted line represents one optional double bond either between the carbon atoms in position 1 and 2 or between the carbon atoms in positions 2 and 3, and
wherein
R
1
represents H or OH, OC(═O)R
5
or OR
5
R
2
, R
3
, which may be the same or different, each represent H, F, Cl, Br, lower (C
1-6
) alkyl, lower (C
2-6
) alkenyl, lower (C
3-6
) cycloalkyl, or CH
2
X (wherein X is F, Cl or Br);
R
4
indicates that the A ring may be (i) unfunctionalised, or (ii) contain a 1,2-double bond or 2,3-double bond, or (iii) contain a 3&agr;- or 3&bgr;-OH, F, Cl or Br group with or without a 1,2-double bond, or (iv) contain a 1&agr;- or 1&bgr;-OH, F Cl or Br group with or without a 2,3-double bond;
R
5
represents C
1
-C
6
-alkyl.
The following compounds are particularly preferred in the preparation of the inventive preparations:
The content of the component a) in the inventive formulations is in the range of from 0.1 to 20, in particular 0.2 to 10% by weight of the formulation.
As component b) the inventive formulations contain
b) up to 99.9% by weight of an formulation additive selected from the group consisting of
b1) the reaction products of triglycerides based on carboxylic acids having 2 to 30 carbon atoms and ethylene oxide and/or propylene oxide in the presence of a base, and/or
b2) fatty acid esters of sugar alcohol polyethoxylates.
The component b1 is obtainable by the reaction of an oil/fat based on a triglyceride of carboxylic acids having 2 to 30 carbon atoms and ethylene oxide and/or propylene oxide in the presence of a base. Fatty acid alkoxylates are primarily formed.
In the triglycerides, three equivalents of carboxylic acid are esterified with glycerol. The carboxylic acids can be saturated or mono- or polyethylenically unsaturated.
Preferably, the present invention uses naturally occurring oils and fats which contain triglycerides as the main constituent. They can be crude, denatured or refined.
Suitable natural oils and fats are: vegetable oils such as olive oil, safflower oil, soybean oil, groundnut oil, cotton oil, corn oil, rape oil, castor oil, sunflower oil, coffee oil, linseed oil, coconut fat and mixtures thereof, animal fats and oils such as fish oils, e.g. sardine oil, herring oil, salmon oil, shark-liver oil or whale oil, and further tallow oil, bone oil, woolfat fractions and bovine tallow.
The following vegetable oils are preferred: castor oil, soybean oil, rape oil and corn oil. Particularly preferred of these is castor oil.
Per mol of the triglyceride on which the oil is based, from 1 to 100, preferably from 10 to 35 and in particular from 15 to 30, mol of ethylene oxide and/or propylene oxide are employed.
Suitable bases are especially inorganic bases such as the alkali metal or alkaline earth metal hydroxides, e.g. sodium hydroxide, potassium hydroxide or calcium hydroxide. Instead of the direct use of hydroxides, it is possible to use carbonates or hydrotalcites, which, if appropriate, were hydrophobized with aliphatic or aromatic carboxylic acids, alcohols having 4 to 22 carbon atoms or the ethoxylates of alcohols of this type, or basic alkaline earth metal phosphates such as strontium phosphate, barium phosphate and calcium phosphate, each of which also form hydroxide ions in the presence of small amounts of water.
The base particularly used is potassium hydroxide.
Per mol of triglyceride, from 0.1 to 5, and in particular from 0.1 to 2, % by weight of base, based on the weight of the triglyceride, are generally added to the reaction mixture.
The reaction is generally carried out at elevated pressure, preferably at from 1 to 10 and in particular at from 1 to 5 bar and at from 80 to 230 and especially from 100 to 150° C.
Working-up is in general carried out such that excess ethylene oxide or propylene oxide is removed under reduced pressure.
Otherwise, the carrying-out of such alkoxylation reactions and the isolation of the resulting reaction products is known to the person skilled in the art (cf.

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