Brassinosteroid biosynthesis inhibitors

Details Brassinosteroid biosynthesis inhibitors Brassinosteroid biosynthesis inhibitors

2001-04-18

2002-05-14

Solola, T. A. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C514S383000

Reexamination Certificate

active

06388089

ABSTRACT:

This application is a 371 of PCT/J99/04380, filed on Sep. 12, 1999.
TECHNICAL FIELD
The present invention relates to a compound having inhibitory action against the brassinosteroid biosynthesis and a plant growth regulator comprising said compound.
BACKGROUND ART
Brassinosteroids have recently recognized as a new class of plant hormones through the combination of molecular genetics and researches on biosyntheses (Yokota, Trends in Plant Sci., 2, pp.137-143, 1997). Since the chemistry of brassinosteroids was established, biological activities of these homologues have been extensively studied, and their notable actions on plant growth have been revealed, which include elongation of stalks, growth of pollen tubes, inclination of leaves, opening of leaves, suppression of roots, activation of proton pump (Mandava and Annu. Rev. Plant Physiol. Plant Mol. Biol., 39, pp.23-52, 1988), acceleration of ethylene production (Schlagnhaufer et al., Physiol. Plant, 61, pp.555-558, 1984), differentiation of vessel elements (Iwasaki et al., Plant Cell Physiol., 32, pp.1007-1014, 1991; Yamamoto et al., Plant Cell Physiol., 38, pp.980-983, 1997), and cell extension (Azpiroz et al., Plant Cell, 10, pp.219-230, 1998).
Furthermore, mechanisms and regulations of physiological actions of brassinosteroids have been being revealed by variety of studies on their biosynthesis (Clouse, Plant J. 10, pp.1-8, 1996; Fujioka et al., Physiol. Plant, 100, pp.710-715, 1997). At present, 40 or more brassinosteroids have been identified. Most of C28-brassinosteroids are common vegetable sterols, and they are considered to be biosynthesized from campesterol which has the same carbon side chain as that of brassinolide.
Some Arabidopsis mutants which show characteristic dwarfism have been isolated, i.e., dwfl: Feldman et al., Science, 243, pp.1351-1354, 1989; dim: Takahashi et al., Genes Dev., 9, pp.97-107, 1995; cbb1: Kauschmann et al., Plant J., 9, pp.701-703, 1996. Their structural photomorphogenesis and dwarfism (cpd; Szekeres et al., Cell, 85, pp.171-182, 1997) and de-etiolation (det2: Li et al., Science, 272, pp.398-401, 1996; Fujioka et al., Plant Cell, 9, pp.1951-1962, 1997) are known. The mutants have deficiencies in the brassinosteroid biosynthetic pathway. Further, a dwarf mutant of
Pisum sativum
was recently characterized, and the mutant was reported as a brassinosteroid deficient mutant (Nomura et al., Plant Physiol., 113, pp.31-37, 1997). In these plants, use of brassinolide is known to negate severe dwarfism of the mutants. Although these findings suggest that roles of brassinosteroids are indispensable for growth and development of plants, an effective tool other than the analysis of mutants has been desired to elucidate physiological importance of brassinolide.
As seen in researches of gibberellin action, specific inhibitors against the biosynthesis are generally very effective tools for elucidating physiological functions of endogenous substances. Specific inhibitors for the brassinosteroid biosynthesis are expected to provide a new tool for understanding the functions of brassinosteroids. Uniconazol is a potent plant growth regulator (PGR) which inhibits the oxidation employed by cytochrome P-450 in the steps of the gibberellin biosynthesis from ent-kaurene to ent-kaurenoic acid. Yokota et al. observed slight reduction of the amount of endogenous castasterone as a side effect of that compound (Yokota et al., “Gibberellin”, Springer Verlag, N.Y., pp.339-349, 1991). Although uniconazole inhibits differentiation of vessel elements induced by brassinolide (Iwasaki et al., Plant Cell Physiol., 32, pp.1007-1014, 1991), its inhibitory action against brassinolide is considered to be no more than an incidental action, because uniconazol essentially inhibits the gibberellin biosynthesis.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a specific inhibitor against the brassinosteroid biosynthesis. Some mutants which are deficient in enzymes for biosynthesis are known for Arabidopsis, and their morphologic changes are unique to mutants with deficiency in the brassinosteroid biosynthesis. Therefore, the inventors of the present invention conducted intensive search for a compound inducing the morphologic changes unique to the mutants with the brassinosteroid biosynthesis deficiency to find a specific inhibitor against the brassinosteroid biosynthesis. As a result, they found that the triazole compounds represented by the following formula (I) had the desired inhibitory action. The present invention was achieved on the basis of these findings.
The present invention thus provides a compound represented by the following formula (I):
wherein R
1
represents a lower alkyl group, R
2
represents a phenyl group which may be substituted or a lower alkyl group, and R
3
represents a phenyl group which may be substituted, or a salt thereof. According to a preferred embodiment of the present invention, there are provided the aforementioned compound or a salt thereof wherein R
1
is methyl group or ethyl group, and R
2
represents a phenyl group which may be substituted or tert-butyl group.
As another aspect of the present invention, there are provided an inhibitor against the brassinosteroid biosynthesis which comprises the compound represented by the aforementioned formula (I) or a physiologically acceptable salt thereof. The inhibitor of the present invention can be used as a plant growth regulator for, for example, suppression of plant elongation, suppression of pollen growth, retention of freshness of flowers, anti-stress agents for plants, weeds control, suppression of plant retrogradation, hypertrophism of roots and so forth.
According to further aspects of the present invention, there are provided a method for regulating plant growth by using the compound represented by the aforementioned formula (I) or a salt thereof; and use of the compound represented by the aforementioned formula (I) or a salt thereof for the manufacture of the aforementioned plant growth regulator.


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Yong Ki Min, et al., “New Lead Compounds for Brassinosteroid Biosynthesis Inhibitors”,Bioorganic&Medicinal Chemistry Letters, 9, pp. 425-430 (1999).
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Mandava,Ann. Rev. Plant Physiol. Plant Mol. Biol., 39, pp. 23-52 (1988).
Schlagnhaufer et al.,Physiol. Plant., 61, pp. 555-558 (1984).
Iwasaki et al.,Plant Cell Physiol., 32 (7), pp. 1007-1014 (1991).
Yamamoto et al.,Plant Cell Physiol., 38 (8), pp. 980-983 (1997).
Azpiroz et al.,The Plant Cell, vol. 10, pp. 219-230 (1998).
Clouse,The Plant Journal, 10 (1), pp. 1-8 (1996).
Fujioka et al.,Physiologia Plantarum, 100, pp. 710-715 (1997).
Feldmann et al.,Science, vol. 243, p. 1351-1354 (1989).
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Kauschmann et al.,The Plant Journal, 9 (5), pp. 701-713 (1996).
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Li et al.,Science, vol. 272, pp. 398-401 (1996).
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