Brassinosteroid derivative and plant growth regulator using the

Details Brassinosteroid derivative and plant growth regulator using the Brassinosteroid derivative and plant growth regulator using the

1995-11-29

1998-06-09

Dentz, Bernard

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

549268, A01N 4322, C07D40708

Patent

active

057633665

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 PCT/JP94/00881 filed May 31, 1994.


TECHNICAL FIELD

The present invention relates to novel brassinosteroid derivatives, and a plant growth regulator using them as active ingredients.


BACKGROUND ART

Brassinolide was discovered from rape pollen as plant growth regulating (1979)!, and ever since the plant growth promoting effects of brassinolide and brassinosteroid analogous compounds have been disclosed ("Brassinosteroids. Chemistry, Bioactivity & Applications." ACS Symposium Series 474, American Chemical Society, Washington, D.C., 1991). In this relation, Japanese Laid-open Patent No.1-125396 was disclosed.
However, brassinolide so far known to have the highest physiological activity and brassinosteroid analogous compounds do not produce stable effects in practical use and have not been actually utilized at the present.
It is hence an object of the invention to present a novel brassinosteroid derivative excellent in practical use in the effect and duration of plant growth promoting action by solving the above problem.


DISCLOSURE OF THE INVENTION

The invention presents a brassinosteroid derivative expressed in formula (I). ##STR2##
The invention also presents a brassinosteroid derivative expressed in formula (II). ##STR3##
Moreover, the invention presents a plant growth regulator containing one type or two types of brassinosteroid derivatives expressed in formula (I) ##STR4## and formula (II) ##STR5## as active ingredient.
Novel brassinosteroid analogous compounds having a plant growth regulating activity expressed as compound (I) and compound (II) and the plant growth regulator containing them as active ingredients, presented by the invention, are useful because they show plant growth regulating actions on various plants with an excellent durability.


BEST MODE OF CARRYING OUT THE INVENTION

The invention is specifically described below. capable of enhancing the yield of dihydroxyl formation of 2.alpha.-position and 3.alpha.-position, by adjusting the amount of reaction agent, when performing catalytic hydroxyl formation of (22E, catalytic amount of osmium tetroxide, in the presence of t-butylhydroperoxide or N-methylmorpholine-N-oxide, in inert gas such as nitrogen and argon. Thus obtained 2.alpha. position, 3.alpha. position dihydroxy forms (IV) are dissolved in pyridine containing 4-dimetnylaminopyridine to react with propionic anhydride or butyric anhydride, and then (V) is obtained in the case of propionic anhydride, or (VI) in the case of butyric anhydride. This (V) or (VI) is dissolved in chlorine derivative organic solvent which is stable in oxidation, and is oxidized in organic peroxide, for example, perbenzoic acid, m-monochloroperbenzoic acid, m-monobromoperbenzoic acid, monoperphthalic acid, trifluoroperacetic acid, and their sodium salt or potassium salt, so that compound (I) is obtained from (V), or compound (II) from (VI). ##STR6##
The compound (I) and compound (II) of the invention exhibit favorable actions on plants. For example, by treating with chemicals in the seed or growing period of plants, growth promoting effect, disease resisting effect, chemical injury lessening effect by herbicide, bactericide or insecticide, chemical injury lessening effect by salts, injury lessening effect by low temperature or high temperature stress, moisture stress lessening effect, and the like may be achieved. By treating with chemicals around the blossoming season of plants, the crop will be increased and the quality will be improved in rice, wheat, corn and other gramineous crops, soybean, kidney bean, and other pulse crops, potato, sugarcane, and other tubers, rape and other brassicaceous crops. When melon, watermelon, cucumber, and other cucurbitaceous crops, or tomato, eggplant, and other solanaceous crops are treated with chemicals, the crop will be increased, and the taste, shape and other quality elements will be enhanced. It is also a feature of these compounds that they have no injury on plants.
When using these compounds as plant growth regulators of crops, the

REFERENCES:
patent: 4961775 (1990-10-01), Takatsuto et al.

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