FR2644784A1 - Solutions of basic salts of 6,7-dihydrobenzoquinolizinecarboxylic acid derivatives for their use in the treatment of plant seeds and seeds thus treated - Google Patents

Abstract

Solutions of basic salts of 6,7-dihydrobenzoquinolizinecarboxylic acid derivatives of formula in which Y is chosen from the set consisting of a lower alkyl, lower alkoxy, halo, hydroxyl, nitro, cyano, trifluoromethyl, amino, lower alkanamido, trifluoroacetamido and lower N,N-dialkylamino radical; each R is chosen from the set consisting of a methyl, ethyl or trifluoromethyl radical; n is an integer with a value 0 to 2, and when n has the value 2, Y can be a methylenedioxy or ethylenedioxy radical fixed to adjacent positions of the ring; m is an integer with a value 0 to 2 and when R is a trifluoromethyl radical, m has the value 1, for their use in the treatment of plant seeds. Application to the treatment of plant seeds, process for the treatment of the said seeds and seeds thus treated.

Description

formule dans laquelle chaque Y est choisi dans l'ensemble constitué par un radical alkyle inférieur, alcoxy inférieur, halogéno, hydroxyle, nitro, cyano, trifluorométhyle, amino, alcanamido inférieur, trifluoroacétamido et N,N-dialkylamino inférieur ; chaque R est choisi dans l'ensemble constitué par un radical méthyle, éthyle et trifluorométhyle ; est un nombre entier valant O à 2 et lorsque n vaut 2, Y peut être un radical méthyléne-dioy ou ethylène-dioxy fixé sur les positions adjacentes du noyau ; m est un nombre entier valant O à 2 et lorsque R est un radical trifluorométhyle m vaut 1.Already known are 6,7-dihydro-benzoquinolizine carboxylic acids and their lower amyl esters, of formula

wherein each Y is selected from the group consisting of lower alkyl, lower alkoxy, halo, hydroxyl, nitro, cyano, trifluoromethyl, amino, lower alkanamido, trifluoroacetamido and lower N, N-dialkylamino; each R is selected from the group consisting of methyl, ethyl and trifluoromethyl; is an integer of 0 to 2 and when n is 2, Y may be a methylene-dioy or ethylene-dioxy radical attached to the adjacent positions of the ring; m is an integer of 0 to 2 and when R is a trifluoromethyl radical m is 1.

 Moreover, these compounds are also and generally known as antibacterial active agents with respect to gram- and gram + bacteria whatever the origin of these bacteria, whether from the animal kingdom or from the plant kingdom, as has already been the case. mentioned in U.S. Patent No. 3,896,131 and in the corresponding French Patent No. 72,46988.

 In vitro, the activity of these products is easy to demonstrate when the bacterium is in contact with the product used. The concentration and contact time parameters are variable with the bacteria.

 In vivo, in humans or animals, in order to be active, the product used must be absorbed into the blood, tissues or body fluids in order to then diffuse at a concentration and duration that vary according to the bacteria, because of the disease.

 For plants, the situation is similar: the product must remain on these at a concentration and duration sufficient to destroy the bacterium.

Thus, for example, the activity of the products mentioned above with respect to
Pseudomonas, Xanthomonas, Erwinia, Corynebacteria,
Aeromonas, phytopathogenic bacteria.

 Different spraying means, at different concentrations, were then tested.

 It has thus been shown that a product belonging to the family of the compounds described above, administered according to the usual processes of atmospheric spraying under normal conditions, that is to say in the absence of lesions or wounds, does not penetrate not inside the plant.

 European Patent Application No. 0,236,230 describes the application of aqueous suspensions of such crystallized products in the form of undissolved needles and acidic pH, to the treatment of aerial parts of plants.

 It is also interesting to treat plant seeds. Indeed, the seeds may look healthy but not develop or give birth to stunted or poorly robust plants.

 The above acidic suspensions specially designed for the treatment of plants have proved to be ineffective for such treatments.

 Therefore, contrary to the ideas received in the field of plant treatment, the Applicant has discovered that the basic salt solutions of 6,7-dihydro-benzoquinolizine-carboxylic acid derivatives described above have outstanding properties in the treatment of plant seeds.

dans laquelle chaque Y est choisi dans l'ensemble constitué par un radical alkyle inférieur, alcoxy inférieur, halogéno, hydroxyle, nitro, cyano, trifluorométhyle, amino, alcanamido inferieur, trifluoroacétamido et N,N-dialkylamino inférieur ; chaque R est choisi dans l'ensemble constitue par un radical méthyle, éthyle et trifluorométhyle ; n est un nombre entier valant 0 à 2, et lorsque n vaut 2, Y peut être un radical méthylènedioxy ou éthylène-dioxy fixé sur les positions adjacentes du noyau ; m~ est un nombre entier valant 0 à 2 et lorsque
R est un radical trifluorométhyle, m vaut 1, pour leur utilisation dans le traitement des semences de végétaux.For this reason, the subject of the present application is the solutions of basic salts of derivatives of 6,7-dibromo-benzoquinolizine-carboxylic acid of formula

wherein each Y is selected from the group consisting of lower alkyl, lower alkoxy, halo, hydroxyl, nitro, cyano, trifluoromethyl, amino, lower alkanamido, trifluoroacetamido and lower N, N-dialkylamino; each R is selected from the group consisting of methyl, ethyl and trifluoromethyl; n is an integer of 0 to 2, and when n is 2, Y may be methylenedioxy or ethylene-dioxy attached to adjacent positions of the ring; m ~ is an integer equal to 0 to 2 and when
R is a trifluoromethyl radical, m is 1, for their use in the treatment of plant seeds.

 By "plant seeds" is meant all plant elements directly used for their reproduction such as seeds, bulbs, roots, rhizomes, cuttings, etc.

 The basic solutions according to the invention therefore find application in particular in the treatment of seeds, bulbs, roots, rhizomes, and cuttings, to protect them from bacterial infections. The reproductive elements thus treated become insensitive to the seeds neutralized by the above-described derivatives and the plant which is developed is itself partially protected because it carries with it said derivatives in its growth.

 The basic salts may be preferably the salts formed with the inorganic bases such as sodium hydroxide, potassium hydroxide or else with organic bases such as ammonia, mono-, tri or triethanolamine and natural or non-natural amino acids. They can be made in a known manner. Solutions can be made directly without isolating the corresponding basic salt.

 In order to improve the treatment of plant seeds by means of the solutions according to the invention, plasticisers are advantageously incorporated in this solution.

 By "plasticizers" is meant plasticizers permeable to water by. for example, those used for coating tablets in human medicine, such as cellulose derivatives such as cellulose acetate phthalate, methylcellulose, ethylcellulose, propylcellulose or hydroxymethylcellulose, or such as derivatives of poly-N-vinylpyrrolidone. like vinyl or polyvinyl resins.

 This is why the present application also relates to the basic salt solutions of 6,7-dihydro-benzoquinolizinecarboxylic acid derivatives as defined above, characterized in that they also contain a plasticizer.

 In some cases, it has been noted that the presence of a surfactant may enhance the effects of the basic salts of the present invention.

 The present application therefore also relates to basic salt solutions of derivatives of 6,7dihydro-benzoquinolizine-carboxylic acid, characterized in that they additionally contain a surfactant.

 By "surfactant" is meant agents capable of modifying the osmotic pressure, for example at the level of the seeds of the seed and promoting osmosis.

Nonionic derivatives such as polyethoxylated alkylphenols, such as those sold under the names Sandozine, Sandovit, may for example be mentioned.
Antarox Co 620 or 630, Renex 698, etc., or ionic, anionic, such as polysorbates such as Tween 60 and 80 or even cationic salts such as quaternary ammonium salts, for example cetylpyridinium or cetyltrimethylammonium halides.

 The plasticizer can be used for example at a concentration of 5 to 30% for seed treatment and preferably at a concentration of 20%.

 The surfactant is advantageously used at a concentration of 0.1 to 3% for seed treatment and preferably at a concentration of 0.5.

 The present application also relates to the application of the basic salt solutions derived from 6,7-dihydro-benzoquinolizine-carboxylic acid, as defined above, to the treatment of plant seeds, in particular to the treatment of seeds, bulbs, roots, tubers and cuttings.

 Examples include pea seeds, beans, soybeans, rice, corn, onion bulbs (alium cepa), endive roots, carrots, beets, potato tubers, cuttings Kiwi.

 For the implementation of the plant seed treatment above, it is preferably carried out by covering said seeds with the aid of said solutions, and then the seeds thus coated are dried.

 This is why the present application also relates to a plant seed treatment process, characterized in that the seeds are covered with a solution as defined above, and then dried seeds thus treated.

 One can operate for example by soaking and drying.

 It can be done by coating then drying or coating and drying simultaneously.

 It operates according to the techniques and with conventional materials, for example those used in the pharmaceutical industry for coating, soaking or drying.

 When it is carried out by soaking, the seeds are advantageously brought into contact for about two hours with the basic salt solution, for example in a tank.

 During a dipping operation, a solution at a concentration of about 300 μg / ml of basic salt derivatives is advantageously used.

 In some cases, for example the cultivation of layered fungi, it is advantageous not to treat the seeds directly but rather to treat the substrate on which the plants are grown.

 Therefore, the present application also relates to a method for treating plant seeds, characterized in that the substrate is treated on or in which the seeds are planted, using a solution as defined above.

 The present application finally relates to seeds characterized in that they are treated using one of the solutions as defined above.

 Examples of implementation of the invention are given below in the experimental part.

 The following examples illustrate this request, but do not limit it.

EXAMPLE 1
Preparation of solutions of sodium salts of fluméqu ine
1 g of flumequine is dissolved in 10 ml of a solution of 0.156 g of sodium hydroxide pellets to obtain 10 mg of a sodium solution with 10 ml of flumequine.

Example 2
Preparation of solutions of potassium salts of flumequine
1 g of flumequine is dissolved in 10 ml of a solution of 0.40 g of potassium hydroxide to obtain a 10% potassium solution of flumequine.

EXAMPLE 3
Preparation of ammoniacal solutions of flumequine
1 g of flumequine is dissolved in 9.3 ml of water and 0.7 ml of ammonia to give 10 ml of a 10% ammonia solution of flumequine.

EXAMPLE 4
Treatment of pea seeds by soaking
1 kg of pea seeds are soaked for two hours in a solution of Example 1.

 Peas are taken and quickly rinsed under running water.

EXAMPLE 5
Coating treatment
The pea or bean seeds are coated in a mixture containing the coating agent and flumequine in the form of an alkaline salt.

 About 40 pea seeds are placed in a mortar containing 0.15 ml of Sepiret 2008 and 0.8 ml of solution containing 0.5% of flumequine sodium salt. Mix until homogeneous coating. These seeds are then allowed to dry on a glass plate for 24 hours at room temperature.

 The remarkable properties in the seed treatment of the basic salt solutions of 6,7-dShydro-benzoquinolizine-carboxylic acid derivatives according to the present invention have been demonstrated according to the conventional method for determining MIC (minimal inhibitory concentration). .

 The agar is inoculated in bulk with one of the many germs sensitive to said derivatives.

 The test samples are then deposited, incubated and the results read. The germ was grown in the agar mass, except around the sample of the tested derivative.

 The inhibition diameter of the culture of the seed is related to the efficiency of the derivative with respect to it and for the same derivative, with the quantity of the product tested.

Müller Hinton agar seeded with Morganella morganii germs, strain of Institut Pasteur CIP A236 or phytopathogenic germs such as Pseudomonas lacrimans, Pseudomonas tomato or
Corynebacterium michiganense. Incubation was 18 hours at 37 ° C for Morganella morganii and 48 hours at 25 ° C for other germs.

 As the derivative of 6,7-dihydro-benzoquinolizinecarboxylic acid, the fluméqugne or the 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H @ tH-benzo (ij) acid was used. quinolizine-2 carboxylic acid.

Example 6
Influence of the acidic or basic form of flumhauine
The activity of flumequine was tested in acidic suspension and in alkaline solution on the bean.

The reference flumequine acidic suspension of this example and the following examples was prepared as follows
A suspension containing 15 μl of flumequine in acid form is diluted to give an acid suspension (HCl) at 300 g / ml of flumequine.

 Beans were soaked for two hours in a solution containing 300 μg / ml of acidic suspension and flumequine alkaline solution.

 Samples of cotyledons and teguments were then collected for testing.

The results obtained are as follows
Table I
Bean: Diameter of the inhibition zone
Soaking time: 2 hours
Basic Solution
Salt of: Sodium Potassium Ammonium acid
Cotyledons 16.8 16.7 19.3 Not detected
Teguments 15.0 13.7 16.8 Not detected
The alkaline solution form allows a much better penetration of the active ingredient than the acid form.

Example 7
Influence of the acidic or basic form of flumequine
The influence of the acidic or basic form has been tested on the potato intended for reproduction.

 The potatoes are soaked in solutions (or suspensions) of flumequine at a concentration of 300 or 600 g / ml for one or two hours.

 After a quick wash with running water, the potatoes are peeled to a thickness of 1 mm to evaluate the degree of diffusion of the derivative inside the tuber. The fragments are then cut with a cookie cutter. of diameter 7 mm. Each fragment tested has a thickness of about 1 to 2 mm.

The results obtained are as follows
Table II
Time concentration. Suspension Solution
Flumequine (; g / ml) Sodium (HCl) Sodium Dipping
1 h 19.57 26.75
2.83 + 1.68
300
2 hours 15.10 23.33
# 0.61 # 0.63
1 h 15.32 31.95
+ 1s02 + 1 41
600
2 h 18.08 29.19
# 1.03 # 2.48
Flumequine and the salts of derivatives of 6,7-dihydro-benzoquinoline-carboxylic acid in acidic suspension diffuse much less easily into the potato than when they are in basic solution.

Example 8
Influence of the acidic or basic form of flumequine
The influence of the acidic or basic form has been tested on pea seeds. The pea seeds are soaked for two hours in a basic solution of flumequine according to Examples 1, 2 and 3 and in an acid suspension of flumequine.

 After rapid rinsing of the seeds with running water, the integuments and cotyledons are separated from the cotyledons. The integuments are cut into small pieces and tested. The incubation was carried out for 24 hours at 37 ° C.

The results obtained are as follows
Table III
Basic solution Acid solution
Teguments 19.25 19.80 19.07 10.59 # 2.69 # 1.07 # 1.48 # 1.88
Cotyledons 11.90 15.90 9.70 Not Detected # 4.88 # 5.90 # 3.66
Flumequine and the salts of 6,7-dihydro-benzoquinolizine carboxylic acid derivatives in basic form are much more active in basic solution than in acid suspension.

Example 9
Influence of soaking time of concentration
The penetration of basic flumequine solutions from the interior of pea or bean seeds was evaluated.

Table IV
A) Seeds of peas @ cotyledons
Flumequine Concentration Time (g / ml)
soaking 150 300 450 600
30 min 8,46 14,86 8,47 18,28 # 1,27 # 5,08 # 1,37 # 5,30
1 hr 10.27 12.99 12.74 13.97 # 1.64 # 4.12 # 1.73 # 3.38
2 hrs 23.50 30.06 29.68 30.00 # 4.65 # 2.86 # 3.52 # 1.43
4 hrs 29.90 30.04 33.23 31.88
# 1,86 +2.07 +2,27 +0.84
6 h 26.27 29.37 28.64 30.55
+2.26 # 2.41 + 2.12 +1.09
Table V
A) Pea seeds: integuments
Flumequine Concentration Time (g / ml)
soaking 150 300 450 600
30 min 19.33 28.63 12.51 27.58 # 2.50 # 0.61 # 2.79 # 0.68
1 h 20.54 24.58 22.46 23.48 # 2.24 # 1.15 # 2.07 # 1.47
2 hrs 31.85 35.89 32.99 34.58 # 1.79 # 3.60 # 3.11 # 3.53
4 h 27.02 28.54 30.14 29.38 # 3.10 # 1.27 # 0.88 # 0.50
6 h 23.92 25.03 27.97 26.10
+1.64 +2.70 +1.09 +0.29
Ideal conditions correspond to a two hour soak in a flumequine solution at a concentration of 300 g / ml.

Table VI
B) Seeds of beans: cotyledons
Flumequine Concentration Time (g / ml)
soaking 150 300 450 600
1 h 21.59 23.53 22.67 24.31 # 2.71 # 2.33 # 2.90 # 2.31
2 hrs 23.27 23.77 24.37 25.59
+2.36 + 2.93- + 1.36 32.31
4 h 25.23 27.21 26.70 26.21
+1.64 # 1.77 +1.48 +3 00
5 hrs 25.32 27.86 27.83 27.13 # 2.14 # 0.92 # 1.51 # 2.30
Table VII
B) Seeds of beans: integuments
Flumequine Concentration Time (μg / ml)
soaking 150 300 450 600
1 hr 22.51 27.29 26.25 25.29 # 2.64 # 2.44 # 2.02 # 1.98
2 hrs 21.53 25.94 27.79 26.95 # 0.91 # 0.86 # 1.11 # 0.58
4 hrs. 22.89 25.83 26.40 26.58
+1.71 - # 2.19 +3.81
5 h 23.62 23.00 27.62 22.58
+0.59 +2.15 # 3.17 +1.15
In the case of beans, it is also the concentration of 300 g / ml for a soaking time of two hours which seems the best choice.

Example 10
Influence of the coating agent
The pea and bean seeds were dipped in a solution containing 0.15 ml of Sepiret 2008 coating agent and 0.8 ml of flumequine sodium solution, immediately removed and then dried for 24 hours at room temperature.

The seeds are then germinated in moist sand. The seeds are then removed after a day, four days and eleven days. The cotyledons are separated from the integuments and the aerial part and the germ are removed. The cotyledons are cut with a cookie cutter diameter 7 mm and the different parts: teguments, aerial parts and germs are cut into small pieces. The assessment is made at the aerial part and the germ, as follows> OO: no detection (<CMI) +: limit detection of flumequine from + to +++: detection of increasing importance
The results obtained are as follows
Table VIII
Spotted

<tb><SEP> TIME <SEP> CONC. <SEP> FROM <SEP> PART
<tb><SEP> OF <SEP> FLUMEQUIN <SEP> COTYLEDON <SEP> TEGUMENT <SEP> AIR <SEP> GERM
<tb> GCRMINATION
<tb><SEP> 1.25 <SEP>% <SEP> 14.85 <SEP>#<SEP> 3.95 <SEP> 18.20 <SEP>#<SEP> 3.86 <SEP> - <September>
<tb><SEP> (27 <SEP>%) <SEP> (21 <SEP>%)
<tb><SEP> 1 <SEP> DAY <SEP> 2.5 <SEP>% <SEP> 16.96 <SEP>#<SEP> 3.09 <SEP> 18.12 <SEP>#<SEP> 3.74 <SEP> - <SEP>
<tb> (18 <SEP>%) <SEP> (21 <SEP>%)
<tb><SEP> 5.0 <SEP>% <SEP> 20.48 <SEP>#<SEP> 2.74 <SEP> 21.37 <SEP>#<SEP> 2.03 <SEP> - <September>
<tb><SEP> (13 <SEP>%) <SEP> (9 <SEP>%)
<tb><SEP> 1.25 <SEP>% <SEP> 7.81 <SEP>#<SEP> 1.24 <SEP> 10.58 <SEP>#<SEP> 1.31 <SEP><0<SEP>#
<tb><SEP> (16 <SEP>%) <SEP> (12 <SEP>%)
<tb> 4 <SEP> DAYS <SEP> 2.5 <SEP>% <SEP> 8.28 <SEP> 3 <SEP> 1.60 <SEP> 8.59 <SEP>#<SEP> 2.11 <SEP><0<SEP> +
<tb><SEP> (19 <SEP>%) <SEP> (25 <SEP>%)
<tb><SEP> 5.0 <SEP>% <SEP> 17.02 <SEP>#<SEP> 4.03 <SEP> 19.16 <SEP>#<SEP> 3.33 <SEP> + <SEP> ++
<tb><SEP> (17 <SEP>%)
<tb><SEP> 1.25 <SEP>% <SEP> ND <SEP> 9.85 <SEP>#<SEP> 3.83 <SEP><0<SEP>#
<tb><SEP> (39 <SEP>%)
<tb> 11 <SEP> DAYS <SEP> 2.5 <SEP>% <SEP> 8.14 <SEP>#<SEP> 1.90 <SEP> 9.99 <SEP>#<SEP> 2.90 <SEP><0<SEP>#
<tb><SEP> (23 <SEP>%) <SEP> (29 <SEP>%)
<tb><SEP> 5.0 <SEP>% <SEP> 11.06 <SEP>#<SEP> 4.55 <SEP><SEP> 14.07 <SEP>#<SEP><SEP> 2, 24 <SEP>#<SEP> +
<tb><SEP> (41 <SEP>%) <SEP> (16 <SEP>%)
<Tb>
Table IX
B) Bean

<tb><SEP> TIME <SEP> CONC. <SEP> FROM <SEP> PART
<tb><SEP> OF <SEP> FLUMEQUIN <SEP> COTYLEDON <SEP> TEGUMENT <SEP> AIR <SEP> GERM
<tb> GERMINATION
<tb><SEP> 1.25 <SEP>% <SEP> 20.34 <SEP>#<SEP><SEP> 1.90 <SEP> 16.41 <SEP>#<SEP> 3.75 <SEP > - <SEP>
<SEP>(<SEP> 9 <SEP>%) <SEP> (23 <SEP>%)
<tb><SEP> 1 <SEP> DAY <SEP> 2.5 <SEP>% <SEP> 21.31 <SEP>#<SEP><SEP> 2.09 <SEP> 18.08 <SEP>#<SEP><SEP> 3.03 <SEP> - <SEP>
<SEP> (10 <SEP>%) <SEP> (17 <SEP>%)
<tb><SEP> 5.0 <SEP>% <SEP> 24.17 <SEP>#<SEP> 0.76 <SEP> 23.79 <SEP>#<SEP> 2.99 <SEP> - <September>
<tb><SEP> (3 <SEP>%) <SEP> (13 <SEP>%)
<tb><SEP> 1.25 <SEP>% <SEP> 13.45 <SEP>#<SEP><SEP> 3.38 <SEP> 18.35 <SEP>#<SEP><SEP> 1, 89 <SEP>#<SEP> +++
<tb> (23 <SEP>%) <SEP> (10 <SEP>%)
<tb><SEP> 4 <SEP> DAYS <SEP> 2.5 <SEP>% <SEP> 15.94 <SEP>#<SEP><SEP> 3.79 <SEP> 18.41 <SEP>#<SEP><SEP> 2.36 <SEP> + <SEP> +++
<tb><SEP> (24 <SEP>%) <SEP> (13 <SEP>%)
<tb><SEP> 5.0 <SEP>% <SEP> 19.31 <SEP>#<SEP><SEP> 2.34 <SEP> 20.81 <SEP>#<SEP><SEP> 2, 23 <SEP> ++ <SEP> +++
<tb><SEP> (12 <SEP>%) <SEP> (11 <SEP>%)
<tb><SEP> 1.25 <SEP>% <SEP> 8.38 <SEP>#<SEP><SEP> 1.61 <SEP> 9.69 <SEP>#<SEP><SEP> 1, 25 <SEP> + <SEP> +
<tb><SEP> (19 <SEP>%) <SEP> (13 <SEP>%)
<tb><SEP> 11 <SEP> DAY <SEP> 2.5 <SEP>% <SEP> 14.19 <SEP>#<SEP><SEP> 4.69 <SE> 15.62 <SEP>#<SEP><SEP> 1.79 <SEP> ++ <SEP> ++
<tb><SEP> (33 <SEP>%) <SEP> (11 <SEP>%)
<tb><SEP> 5.0 <SEP>% <SEP> 15.85 <SEP>#<SEP><SEP> 3.81 <SEP> 19.80 <SEP> 3 <SEP> 2.03 <SEP > ++ <SEP> ++
<tb><SEP> (24 <SEP>%) <SEP> (10 <SEP>%)
<Tb>
After germination, the seeds coated in the flumequine-coating agent mixture show the presence of the active ingredient in both the cotyledons and the integuments.

 there was penetration whereas the seeds were only immersed in the solution to be tested. Sprouting allowed penetration of the active ingredient into the seed.

Example 11
Treatment of other reproductive elements
a) Reproduction by cuttings
For a number of plants, normal reproduction is not possible or difficult and propagation must be by cuttings. Pre-treatment of cuttings with alkaline or basic flumequine solutions results in more vigorous plants and more easily rooted cuttings. A substantially similar effect is obtained by treatment, not of the cutting itself but of the medium in which the cutting is planted.

b) Culture on artificial synthetic media and wet layers
The cultures of meristems or whole plants on synthetic media, hydroponics, wet mushroom cultures of Paris mushrooms have been greatly improved by treatment of the culture medium itself.

 Flumequine and the salts of 6,7-dihydro-benzoquinolizine-carboxylic acid derivatives have a remarkable effect in germination, rooting and growth.

 The figures in the appendix show the characteristic infrared spectra of the basic salts of flumequine.

Claims (16)

 1. Basic salt solutions of 6,7-dihydro-benzoquinolizine carboxylic acid derivatives of the formula

 wherein each Y is selected from the group consisting of lower alkyl, lower alkoxy, halo, hydroxyl, nitro, cyano, trifluoromethyl, amino, lower alkanamido, trifluoroacetamido and lower N, N-dialkylamino; each R is selected from the group consisting of methyl, ethyl and trifluoromethyl; n is an integer of 0 to 2, and when n is 2, Y may be methylenedioxy or ethylene-dioxy attached to adjacent positions of the ring; m is an integer of 0 to 2 and when R is a trifluoromethyl radical, m is 1, for their use in the treatment of plant seeds.  2. Solutions of basic salts of the derivatives of 6,7-dihydro-benzoquinolizine-carboxylic acid according to claim 1, for their use in the treatment of seeds or bulbs.  3. Basic salt solutions of the 6,7-dihydro-benzoquinolizine-carboxylic acid derivatives according to claim 1 for use in the treatment of roots or rhizomes.  4. Basic salt solutions of the 6,7-dihydro-benzoquinolizine-carboxylic acid derivatives according to claim 1 for use in the treatment of cuttings.  5. Basic salt solutions of the derivatives of 6,7-dihydro-benzoquinolizine-carboxylic acid according to any one of claims 1 to 4, characterized in that they further contain a plasticizer.  6. Basic salt solutions of 6> 7-dihydro-benzoquinolizine-carboxylic acid derivatives according to any one of claims 1 to 5, characterized in that they further contain a surfactant.  7. Application of the basic salt solutions of the 6,7-dihydro-benzoquinolizine-carboxylic acid derivatives as defined in any one of claims 1 to 6, to the treatment of plant seeds.  8. Application of the basic salt solutions of the 6,7-dihydro-benzoquinolizine-carboxylic acid derivatives according to any one of claims 1 to 6 to the treatment of seeds or bulbs.  9. Application of the basic salt solutions of the 6,7-dihydro-benzoquinolizine-carboxylic acid derivatives according to any one of claims 1 to 6, to the treatment of roots or rhizomes.  10. Application of the basic salt solutions of the 6,7-dihydro-benzoquinolizinecarboxylic acid derivatives according to any one of claims 1 to 6 to the treatment of cuttings.  He. A method of treating seed of plants, characterized in that the seeds are covered with a solution according to any one of claims 1 to 6, and then dried seeds so treated.  12. A method of treating plant seeds according to claim 11, characterized in that the seeds are covered by dipping.  13. A method of treating plant seeds according to claim 11, characterized in that the seeds are covered by coating.  14. A method of treating plant seeds according to claims 11 or 12, characterized in that the seeds are covered by soaking for about 2 hours.  15. A method of treating plant seeds according to claims 11, 12 or 13, characterized in that the seeds are covered by soaking in a concentrated solution of about 300 μg / ml.  16. A method of treating seed of plants, characterized in that the substrate is treated on or in which the seeds are planted with a solution as defined in one of claims 1 to 6.  17. Seeds characterized in that they are treated using one of the solutions as defined in any one of claims 1 to 6.