Use of benzo[C]quinolizine derivatives as plant...

Details Use of benzo[C]quinolizine derivatives as plant... Use of benzo[C]quinolizine derivatives as plant...

2000-01-10

2003-02-04

Huang, Evelyn Mei (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S095000, C514S294000

Reexamination Certificate

active

06514912

ABSTRACT:

SCOPE OF INVENTION
The present invention regards the use of benzo[c]quinolizine derivatives of general formula (I)
in which:
R
1
, R
2
, R
3
, R
4
and R
6
, which are the same or different from one another, are chosen from the group consisting of H, C
1-8
alkyl, C
2-8
alkenyl, C
2-8
alkynyl, C
3-6
cycloalkyl, aryl, heterocycle, halogen, CN, azide, NRR′, C
1-8
alkylamine, arylamine, C
1-8
alkyloxy, aryloxy, COOR, and CONRR′, where R and R′, which are the same or different from one another, are chosen from the group consisting of H, C
1-8
alkyl, aryl, heterocycle, aryl-C
1-8
alkyl, and cyclo-alkyl; R
5
is chosen from the group consisting of H, C
1-8
alkyl, aryl-C
1-8
alkyl, COOR, CN, aryl, heterocycle, and the C
1-8
alkyl heterocycle;
X is chosen from the group consisting of O, C(═O)R, COOR, NO
2
, and CONNR′, in which R and R′ are as defined above; Q is chosen from the group consisting of single-bond, C
1-8
alkyl, C
2-8
alkenyl, C
2-8
alkynyl, cyclo-alkyl, CO, CONR, and NR, where R is as defined previously;
W is chosen from the group consisting of H, C
1-8
alkyl, C
2-8
alkenyl, C
2-8
alkynyl, cycloalkyl, trifluoromethyl, C
1-8
alkoxy, C
1-8
alkoxy-C
1-8
alkyl, aryl-C
1-8
alkyl, aryl, aryloxy, arylamine, C
1-8
alkyl-carbonyl, arylcarbonyl, halogen, CN, NRR′, C
1-8
alkylamine, and heterocycle, in which the alkyl, alkenyl, alkynyl, cyclo-alkyl, aryl, and heterocycle groups may be substituted:
n is 1, 2, 3, or 4;
the mark
-------
indicates that the respective bonds a,b,c,d,e,f, and g are single or double bonds, considering that when b or f are a double bond, the R
5
group is absent.
The salts of the compounds of formula (I) are also included in the invention.
STATE OF THE ART
It is known that steroidal enzymes have a considerable importance both in the field of medicine and in that of sciences related to the development of agriculture and foodstuffs. However, whilst the physiological role of steroids in man has been amply studied and documented, the physiological role of steroids in the vegetable world is less well known.
The growth of plants is governed by complex interactions between environmental signals and internal factors. Light regulates many processes of development throughout the life cycles of the plant, starting from seed germination right up to flower development (J. Chory, Trends, Genet., 1993, 9, 167). In the presence of light, the growth of hypocotyledons is inhibited, cotyledons expand, leaves develop, chloroplasts differentiate producing chlorophyll, and a large number of light-inducible genes are activated.
It has been recently suggested that brassinosteroids, which are the most widespread steroids in higher plants, may be directly involved in the response of plants to light (Chory et al., Proc. Natl. Acad. Sci. 1996, 93, 12066). However, the interactions between phototransduction and hormones are not yet well known. Brassinolid is the steroid that has a fundamental role in the development of plants under the effect of light and has been identified in the larger part of higher plants. It is generated through a metabolic cascade in which campesterol (a compound similar to cholesterol) is reduced to campestanol. The enzyme which is responsible for this reduction is a 5-alpha-reductase steroidal enzyme, named DET2 after the gene of the same name isolated for the plant Arabidopsis, which presents a sequence analogy of up to 80% on the conservative amino acids of the iso-enzymes 1 and 2 of the 5-alpha-reductase of humans and rats. The genetic mutations that inactivate DET2 do not allow production of brassinolid and determine deep alterations in the development of seeds and in Arabidopsis plants in the dark or under the effect of light.
In the dark, the plants mutated genetically in DET2 present short and thick hypocotyledons, accumulate anthocyanins, have open and expanded cotyledons, and develop primary-leaf buds. In the light, the mutated plants are smaller and of a darker green, have a reduced apical dominance and male fertility. In addition, they have different responses to light, with delayed flowering and delayed ageing of leaves and chlorophyll (J. Li et al., Science, 1996, 272, 398).
These alterations of the mutating species are reversed with the exogenous addition of brassinolid to the growth medium (J. Li et al., Proc. Natl. Acad. Sci., 1997, 94, 3554-3559).
DETAILED DESCRIPTION OF THE INVENTION
It has now been surprisingly found that the products of formula (I) as described above exert an inhibiting action on the 5-alpha-reductase steroidal enzymes, in particular on the DET2 enzyme, and hence are able to affect selectively the growth of plants in the dark and in the light, and can therefore be used as phytopharmaceutical substances in the field of agriculture and foodstuffs both as substances capable of improving the morphogenesis and development of plants that are commercially useful and as potential herbicides that inhibit the development of weeds.
In the products of formula (I) according to the present invention, by C
1-8
, alkyl, C
1-8
, alkenyl and C,
1-8
alkynyl group are meant alkyl radicals, either linear or branched, such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, ethylene, propene, butene, isobutene, acetylene, propyne, butyne, etc.
By the term cyclo-alkyl the following are meant: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclo-octane, norbornane, camphane, and adamantane.
By the term aryl the following are meant: phenyl and naphthyl.
By the term heterocycle the following are meant in particular: saturated or aromatic heterocycles containing one or more nitrogen atoms, and more in particular, pyridine, imidazole, pyrrole, indole, triazoles, pryrrolidine, and piperidine.
By halogen the following are meant: fluorine, chlorine, bromine, and iodine.
The substituents of the aforementioned W groups are preferably: halogen, OR, phenyl, NRR′, CN, COOR, CONRR′, and C
1-8
alkyl (in which R and R′ are as defined above).
In particular, according to the present invention the products of formula (I) are preferred in which:
R
5
=H, heterocycle, aryl-C
1-8
, alkyl, or C
1-8
alkyl heterocycle;
X=0;
Q=single-bond, CO, CONR, or NR (where R is as defined above);
W=H, F, Cl, Br, Me, tert-butyl, C
1-8
, alkoxy, 2,5-dimethylhexyl, trifluoromethyl, 2,5-(di-trifluoromethyl)-phenyl, 4-methoxy-phenyl, 4-fluoro-phenyl, phenyl, phenyl-C
1-8
alkyl, C
1-8
alkylcarbonyl, or phenylcarbonyl;
n=1 or 2;
R
1
, R
2
, R
3
, R
4
, R
6
=H, Me, CN, phenyl, COOR, or CONRR′(where R and R′ are as defined above).
Products preferred according to the present invention are:
1,2,4,4a,5,6 hexahydro-(11H)-benzo[c]quinolizin-3-one;
8-chloro-1,2,4,4a,5,6 hexahydro(11H)-benzo[c]quinolizin-3-one;
1,2,4,4a,5,6 hexahydro-8-methyl(11H)-benzo[c]quinolizin-3-one;
1,2,4,4a,5,6 hexahydro-4-methyl-(11H)-benzo[c]quinolizin-3-one;
1,2,4,4a,5,6 hexahydro-1-methyl-( 11H)-benzo[c]quinolizin-3-one;
1,2,5,6-tetrahydro-(11H)-benzo[c]quinolizin-3- one;
8-chloro-1,2,5,6-tetrahydro-(11H)-benzo[c]quinolizin-3-one;
8-methyl-1,2,5,6-tetrahydro-( 11H)-benzo[c]quinolizin-3-one;
4-methyl-1,2,5,6-tetrahydro-( 11H)-benzo[c]quinolizin-3-one;
1-methyl-1,2,5,6-tetrahydro-( 11H)-benzo[c]quinolizin-3-one;
4 ,4a, 5,6-tetrahydro-(11H)-benzo[c]quinolizin-3-one;
4a-benzyl4,4a,5,6-tetrahydro-(11H)benzo[c]quinolizin-3-one;
8-chloro4a-benzyl -4,4a,5,6-tetrahydro-(11H)-benzo [c]quinolizin-3 -one;
5,6-dihydro-(11H)benzo[c]quinolizin-3-one;
8-chloro-4,4a,5,6-tetrahydro-(11H)-benzo[c]quinolizin-3-one;
8-chloro-1-methyl-4,4a,5,6-tetrahydro-(11 H)-benzo[c]quinolizin-3-one;
8-methyl4,4a,5,6-tetrahydro-(11 H)-benzo[c]quinolizin-3-one;
(cis) and (trans) 4-methyl4,4a,5,6-tetrahydro-( 11H)-benzo[c]quinolizin-3-one; 8-chloro4-methyl-1 ,2,5,6-tetrahydro-(11H)-benzo&l

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