WO2017158225A1 - Uso de aminoácidos cíclicos no prolínicos para aumentar la tolerancia de plantas a condiciones de estrés osmótico - Google Patents
Uso de aminoácidos cíclicos no prolínicos para aumentar la tolerancia de plantas a condiciones de estrés osmótico Download PDFInfo
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- WO2017158225A1 WO2017158225A1 PCT/ES2017/070153 ES2017070153W WO2017158225A1 WO 2017158225 A1 WO2017158225 A1 WO 2017158225A1 ES 2017070153 W ES2017070153 W ES 2017070153W WO 2017158225 A1 WO2017158225 A1 WO 2017158225A1
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- formula
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- 0 CC1CC(C(*)=O)N*CC1 Chemical compound CC1CC(C(*)=O)N*CC1 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/06—Nitrogen directly attached to an aromatic ring system
Definitions
- the present invention relates to the use of organic molecules to increase the tolerance of plants to conditions of osmotic stress caused by the difficulty in accessing the water in the environment, such as those caused by saline stress or water deficit. Based on the foregoing, this invention can be included in the area of the application of compounds and substances to favor the development of plants under the described conditions of osmotic stress.
- Physiological drought occurs when soluble salts are found in high concentrations in the soil solution, limiting water intake by the plant due to the low water potential that is generated.
- osmotic stress occurs in plants, which results in the generation of a very similar physiological, biochemical and molecular response that affects their development (Sairam and Tyagi, 2004. Current Science 86 (3), 407-421). It is known that plants, and as a survival strategy in these stress situations, can adjust their osmotic potential by generating a lower water potential than that of the soil solution, in order to access the water present in it (Munns and Tester, 2008 Annual Review of Plant Biology 59: 651-681).
- amino acids specifically the non-proline cyclic amino acids of general formula (I), as an example of which include pipecolinic acid and pyroglutamic acid, are capable of stimulating Natural mechanisms of plants that allow them to overcome osmotic stress conditions, significantly increasing their biomass production in these adverse conditions and bringing it closer to the values of control plants not subjected to such stress (see example 2). They have also observed the effect of stimulating these amino acids on the use of water from plants treated with them in situations of osmotic stress caused by water deficit (see example 5). The inventors have also verified that the use of other different amino acids, used in the same conditions of experimentation, do not achieve a recovery of biomass production with respect to a control or if they achieve it is to a lesser extent (see examples 1 to 5) .
- the invention relates to the use of at least one compound of formula (I) to increase the tolerance of plants to conditions of osmotic stress
- n represents an integer between 0 and 1;
- X represents -OH, -0-Ci. 4 alkyl or -NH-Ci_ 4 alkyl; Y
- Z represents H, -OH, -SH or -S-Ci_ 4 alkyl
- n a number between 0 and 1;
- X represents -OH, -0-Ci_ 4 alkyl or -NH-Ci_ 4 alkyl
- n a number between 0 and 1;
- X represents -OH
- the invention relates to the use of a compound of formula (I) as defined above where the compound of formula (I) is the compound of formula (II).
- the invention in another embodiment relates to the use of a compound of formula (I) as defined above where the compound of formula (I) is the compound of formula (III).
- Some compounds of formula (I) have chiral centers that give rise to several stereoisomers.
- the present invention describes each of these stereoisomers and mixtures thereof.
- the "conditions of osmotic stress” are caused by a difficulty in accessing the water available in the environment that houses a plant and that the expert in the state of the art knows as a common element to circumstances of meteorological, agricultural, hydrological drought ( situations of water deficit) or physiological (salinity situations), and that has similar effects on the activation of defense mechanisms of the plant and on the decline of its development (Sairam and Tyagi, 2004. Current Science 86 (3), 407 -421).
- the invention relates to the use of a compound of formula (I) as defined above to increase tolerance to osmotic stress caused by a water deficit. In another embodiment the invention relates to the use of a compound of formula (I) as defined above to increase tolerance to osmotic stress produced by salinity.
- some of the compounds of the present invention may exist as several diastereoisomers and / or several optical isomers.
- the diastereoisomers can be separated by conventional techniques such as chromatography or fractional crystallization.
- Optical isomers can be resolved by conventional optical resolution techniques to give optically pure isomers. This resolution can be carried out in any of the intermediate products of a compound of formula (I).
- Optically pure isomers can also be obtained individually using enantioselective synthesis.
- the present invention covers all individual isomers as well as mixtures thereof (for example racemic mixtures or mixtures of diastereoisomers), both obtained by synthesis and by physical mixing thereof.
- the invention in a second aspect, relates to a method for improving tolerance to osmotic stress conditions, hereinafter method of the invention, which comprises administering to the plant an effective dose of at least one compound of formula (I) such and as defined above.
- the method of the invention comprises using the compound of formula (I) in aqueous solution .
- the method of the invention also comprises using the amino acid of the invention together with various vehicles and agents that facilitate its conservation, handling and application.
- the invention relates to the method defined above where the compound of formula (I) can be used in conjunction with another active ingredient.
- additional active ingredient are, by way of indication and not limitation, nematicides, insecticides, acaricides, fungicides, bactericides, herbicides, growth regulators, fertilizers, synergists, fertilizers and soil conditioners, and preferably where the additional active ingredient is selected from nematicide, insecticide, acaricide, fungicide, bactericide and herbicide.
- the addition of only one of the amino acids of the invention causes beneficial effects on increasing tolerance to situations of osmotic stress, increasing its biomass production to values very similar to those of plants that are not subjected to this stress, the invention It also includes the simultaneous combination of more than one compound of formula (I), such as the compound of formula (II), also referred to as pipecolinic acid, and the compound of formula (III), also referred to as pyroglutamic acid.
- compound of formula (II) such as the compound of formula (II), also referred to as pipecolinic acid
- the compound of formula (III) also referred to as pyroglutamic acid.
- the method of the invention is applicable to increase the tolerance to osmotic stress caused by a water or salinity deficit.
- Ci. 4 alkyl as a group or part of a group, means a straight or branched chain alkyl group containing 1 to 4 C atoms; and includes the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and te / f-butyl groups.
- plant means indistinctly both an individual and a plurality thereof, whether considered in its entirety, that is, including aerial part and radical part irrespective of their stage of development, or partially considered , that is, any portion thereof that can be used as plant material for reproduction or multiplication.
- Plant breeding material means both the seed and the fruit that comprises it.
- Multiplication plant material means any fragment of a plant from which at least one new specimen can be obtained and which is normally used as a basis in propagation techniques, such as propagation by layers, cuttings, stakes, stolons, buds, rhizomes, tubers, bulbs or corms; graft propagation; micropropagation; or propagation by in-vitro culture.
- propagation techniques such as propagation by layers, cuttings, stakes, stolons, buds, rhizomes, tubers, bulbs or corms; graft propagation; micropropagation; or propagation by in-vitro culture.
- the most suitable techniques may include spraying the amino acid of the invention on the leaves, or injection into the stem, while for the root part, the application It can be done by incorporation into the irrigation water or the substrate that houses the plant.
- the radical part in a solution comprising the amino acid of the invention or the total immersion of the plant material, either of reproduction or multiplication.
- the application is by immersion of the radical part.
- Examples of cultivation in which the method of the invention can be applied are any monocot or dicot crop, for indicative and non-limiting purposes, cereal, fruit, vegetable, vegetable, or ornamental plant crops.
- an example of cultivation is tomato.
- the invention relates to the method as defined above, which comprises the application in aqueous solution of the compound of formula (I) by immersion of the root system.
- the invention relates to the method as defined above, which comprises the application in aqueous solution of the compound of formula (I) by immersion of the seeds.
- the invention relates to the method as defined above, wherein the compound of formula (I) is the compound of formula (II).
- the invention relates to the method as defined above, wherein the compound of formula (I) is the compound of formula (III).
- the "effective dose” may optionally increase or decrease according to the amino acid of the selected invention, of the plant material, of its stage of development, of the type of formulation, of the time, of the place, of the frequency of application and of the degree of osmotic stress .
- the amino acid of the invention is used in a concentration range of 0.1 ⁇ to 3 M.
- FIGURES Fig. 1 Represents a scheme showing the culture conditions during the test.
- Fig. 2. Represents the weight of tomato plants after 7 days of growth in the different solutions. * Significant differences with respect to the control group with the same treatment with a p value ⁇ 0.05; ** Significant differences with respect to the control group with the same treatment with a p value ⁇ 0.01.
- the conditions described below were used as the basis for all the examples included below.
- the culture conditions, such as the nutrient solution and the substrate used, have been optimized for carrying out this type of experiments.
- the dose of NaCi used has been optimized for this type of experiments since 50 mM allows to assess whether a treatment is capable of increasing salinity tolerance (Jiménez-Arias ef al., 20 5. Environmental and Experimental Botany 120.23-30).
- hydroponic culture system For the cultivation of the Arahidopsis thaiiana plants necessary for the tests, a hydroponic culture system was used. This system was established in hydroponic cuvettes with 1.9 L capacity (Araponics®) where 18 plants were grown per container. A mixture of river sand of two different particle sizes was used as a physical substrate.
- seed-olders seed-olders
- seed-olders seed-olders
- a small greenhouse consisting of a high-density polyethylene tray with river sand (washed siliceous sand, with medium grating) with distilled water sterile covered with a transparent plastic sheet, which was deposited in a culture chamber at 22 ⁇ 2 o C, with a photoperiod of 16 hours of light (100-1 10 ⁇ m-2 s- of PAR) and with 100% relative humidity
- the seed-holders with the seedlings were transferred to the hydroponics trays under the same photoperiod and light intensity conditions, but with 60-70% relative humidity.
- the seedlings were kept without aeration during the first week, from which the solution (Table 1) was generously aerated by aeration pumps and was renewed every 7 days.
- Table 1 Hydroponic solution used in the experiments
- Example 1 Effect of alanine on the response of A. thal ⁇ ana to saline stress caused by the addition of aCI
- a simple amino acid such as alanine was used.
- Table 2 shows the results of the amino acid alanine on plant development.
- Table 2 Effects of alanine on growth in optimal and saline conditions.
- 21-day plants were treated for 24 hours in nutrient solution enriched with a concentration of 2.5 mM pyrogoglutamic acid or pipecolinic acid. Subsequently, the plants were deposited in normal nutrient solution for 24 hours and afterwards they grew for 7 days in nutrient solution with or without a 50 mM NaCI contribution. This experiment was repeated twice, using 12 plants per experiment, the value shown in Table 2 being the average of 24 plants for each of the conditions.
- the salt again significantly decreased the growth, as shown by the fresh weight and the relative growth rate of the plant, after one week of being subjected to saline stress. This did not occur in a significant way in those plants that were previously treated with 2.5 mM of pyrogoglutamic acid or with 2.5 mM of pipecolinic acid, so its effect on increasing tolerance to saline stress is proven.
- the second measure is a percentage of reduction of the relative growth rate of the plant subjected to saline stress conditions.
- Table 4 shows the results. Table 4: Effects of pyroglutamic acid, pipecolinic acid or hydroxyproline on the sensitivity index
- TCR (TCRs-TCRc TCRc) x100; TCRs being growth rate of plants grown under saline conditions; TCRc growth rate of plants grown under control conditions).
- the data shown are the average of two independent experiments with 24 plants in total. The ** show significant differences with respect to the control group with a p ⁇ 0.01.
- the crop used was the tomato (Solanum / ycopersicum) of the "Gransol" black layer.
- the experiment was conducted in a glass greenhouse with four tables 10 meters long by 2 wide. Drip irrigation was used, supplied by self-compensated drippers to control the flow of water at all times.
- Seedlings with five weeks of age were transplanted into pots of 2 liters capacity using a mixture of peat and river sand to facilitate drainage. In total, 120 tomato plants were used. After the transplant, four treatments (spaced every 15 days) were carried out on 40 plants, adding 50 ml of a 2.5 mM Pyroglutamic concentration to each pot. Another 40 plants were treated by root applications using 2.5 mM of pipecolinic acid. The rest of Plants randomly distributed throughout the greenhouse were treated with distilled water as a control. At the end of the four treatments, the drought test began, which was carried out by removing the dropper to 20 plants chosen randomly for each of the treatments. The plants were deprived of water for 10 days. The relative water content of the leaf was estimated at 10 days of drought for each of the treatments, under control conditions and drought conditions, using 15 leaves. For this, the following formula was used:
- the CHR is the most widely used measure to estimate the possible water deficit of a plant leaf.
- the data of the different variables were subjected to the normality test using the Kolmogorov-Smirnov test with the Lilliefors correction.
- the Levene test was used to verify the homocedasticity of the data. As the data behaved following a normal distribution, their means were compared using one-way ANOVA and the significant differences were calculated using the Bonferroni post hoc test. Statistical analyzes were performed with the SSPS version 20 software package for Windows.
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- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cultivation Of Plants (AREA)
- Pyrrole Compounds (AREA)
- Fertilizers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Soil Conditioners And Soil-Stabilizing Materials (AREA)
Abstract
Description
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Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES17765908T ES2898638T3 (es) | 2016-03-17 | 2017-03-17 | Uso de ácido (l)-piroglutámico para aumentar la tolerancia de plantas a condiciones de estrés osmótico |
BR112018068809-6A BR112018068809B1 (pt) | 2016-03-17 | 2017-03-17 | Método para aumentar a tolerância de plantas a condições de estresse osmótico |
EP17765908.3A EP3430905B1 (en) | 2016-03-17 | 2017-03-17 | Use of (l)-pyroglutamic acid to increase the tolerance of plants to conditions of osmotic stress |
US16/085,465 US20190159449A1 (en) | 2016-03-17 | 2017-03-17 | Use of non-proline cyclic amino acids to increase the tolerance of plants to conditions of osmotic stress |
MX2018011301A MX2018011301A (es) | 2016-03-17 | 2017-03-17 | Uso de aminoacidos ciclicos no prolinicos para aumentar la tolerancia de plantas a condiciones de estres osmotico. |
HRP20211694TT HRP20211694T1 (hr) | 2016-03-17 | 2017-03-17 | Uporaba (l)-piroglutamske kiseline za povećanje tolerancije biljaka na uvjete osmotičkog stresa |
PE2018001818A PE20190167A1 (es) | 2016-03-17 | 2017-03-17 | Uso de aminoacidos ciclicos no prolinicos para aumentar la tolerancia de plantas a condiciones de estres osmotico |
ZA2018/06903A ZA201806903B (en) | 2016-03-17 | 2018-10-16 | Use of non-proline cyclic amino acids to increase the tolerance of plants to conditions of osmotic stress |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES201630317A ES2638213B1 (es) | 2016-03-17 | 2016-03-17 | Uso de aminoácidos cíclicos no prolínicos para aumentar la tolerancia de plantas a condiciones de estrés osmótico |
ESP201630317 | 2016-03-17 |
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WO2017158225A1 true WO2017158225A1 (es) | 2017-09-21 |
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PCT/ES2017/070153 WO2017158225A1 (es) | 2016-03-17 | 2017-03-17 | Uso de aminoácidos cíclicos no prolínicos para aumentar la tolerancia de plantas a condiciones de estrés osmótico |
Country Status (11)
Country | Link |
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US (1) | US20190159449A1 (es) |
EP (1) | EP3430905B1 (es) |
BR (1) | BR112018068809B1 (es) |
CL (1) | CL2018002634A1 (es) |
ES (2) | ES2638213B1 (es) |
HR (1) | HRP20211694T1 (es) |
MX (1) | MX2018011301A (es) |
PE (1) | PE20190167A1 (es) |
PT (1) | PT3430905T (es) |
WO (1) | WO2017158225A1 (es) |
ZA (1) | ZA201806903B (es) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020193819A1 (es) * | 2019-03-27 | 2020-10-01 | Fertinagro Biotech, S.L. | Composición fertilizante que incluye un potenciador de potasio asimilable por las plantas y utilización de la misma |
US20200367495A1 (en) * | 2017-11-15 | 2020-11-26 | Heinrich Heine Universitaet Duesseldorf | Method for inducing acquired resistance in a plant |
US20210345611A1 (en) * | 2018-08-28 | 2021-11-11 | Verdesian Life Sciences U.S., Llc | Extended and continuous release compositions for plant health and method of use |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150051072A1 (en) * | 2013-08-16 | 2015-02-19 | Los Alamos National Security, Llc | Compounds And Methods for Improving Plant Performance |
WO2015107336A1 (en) * | 2014-01-14 | 2015-07-23 | Crop Intellect Ltd. | Agrochemical composition comprising a ν,ν'-disubstituted (thio)urea for the improvement of crop productivity |
US20160037772A1 (en) * | 2014-08-08 | 2016-02-11 | Mario Miguel Guerrero Mendez | Increasing abiotic stress tolerance in plants |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US8551917B2 (en) * | 2005-11-07 | 2013-10-08 | Los Alamos National Security, Llc | Use of prolines for improving growth and/or yield |
ITMI20060434A1 (it) * | 2006-03-10 | 2007-09-11 | Arterra Bioscience S R L | Metodo per la preparazione di una composizione a base di 4-idrossiprolina e suoi usi in campo agronomo |
-
2016
- 2016-03-17 ES ES201630317A patent/ES2638213B1/es not_active Expired - Fee Related
-
2017
- 2017-03-17 MX MX2018011301A patent/MX2018011301A/es unknown
- 2017-03-17 US US16/085,465 patent/US20190159449A1/en not_active Abandoned
- 2017-03-17 WO PCT/ES2017/070153 patent/WO2017158225A1/es active Application Filing
- 2017-03-17 ES ES17765908T patent/ES2898638T3/es active Active
- 2017-03-17 EP EP17765908.3A patent/EP3430905B1/en active Active
- 2017-03-17 HR HRP20211694TT patent/HRP20211694T1/hr unknown
- 2017-03-17 PE PE2018001818A patent/PE20190167A1/es unknown
- 2017-03-17 BR BR112018068809-6A patent/BR112018068809B1/pt active IP Right Grant
- 2017-03-17 PT PT177659083T patent/PT3430905T/pt unknown
-
2018
- 2018-09-13 CL CL2018002634A patent/CL2018002634A1/es unknown
- 2018-10-16 ZA ZA2018/06903A patent/ZA201806903B/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150051072A1 (en) * | 2013-08-16 | 2015-02-19 | Los Alamos National Security, Llc | Compounds And Methods for Improving Plant Performance |
WO2015107336A1 (en) * | 2014-01-14 | 2015-07-23 | Crop Intellect Ltd. | Agrochemical composition comprising a ν,ν'-disubstituted (thio)urea for the improvement of crop productivity |
US20160037772A1 (en) * | 2014-08-08 | 2016-02-11 | Mario Miguel Guerrero Mendez | Increasing abiotic stress tolerance in plants |
Non-Patent Citations (1)
Title |
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See also references of EP3430905A4 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20200367495A1 (en) * | 2017-11-15 | 2020-11-26 | Heinrich Heine Universitaet Duesseldorf | Method for inducing acquired resistance in a plant |
US20210345611A1 (en) * | 2018-08-28 | 2021-11-11 | Verdesian Life Sciences U.S., Llc | Extended and continuous release compositions for plant health and method of use |
WO2020193819A1 (es) * | 2019-03-27 | 2020-10-01 | Fertinagro Biotech, S.L. | Composición fertilizante que incluye un potenciador de potasio asimilable por las plantas y utilización de la misma |
Also Published As
Publication number | Publication date |
---|---|
ES2898638T3 (es) | 2022-03-08 |
BR112018068809A2 (pt) | 2019-01-22 |
CL2018002634A1 (es) | 2018-12-28 |
US20190159449A1 (en) | 2019-05-30 |
BR112018068809B1 (pt) | 2022-09-06 |
ZA201806903B (en) | 2024-09-25 |
ES2638213B1 (es) | 2018-07-27 |
MX2018011301A (es) | 2019-07-04 |
EP3430905A4 (en) | 2019-09-04 |
EP3430905B1 (en) | 2021-09-01 |
PE20190167A1 (es) | 2019-02-01 |
HRP20211694T1 (hr) | 2022-02-04 |
EP3430905A1 (en) | 2019-01-23 |
ES2638213A1 (es) | 2017-10-19 |
PT3430905T (pt) | 2021-09-21 |
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