EP1100330A1 - Traitement de plantes au moyen d'acide salicylique et d'amines organiques - Google Patents

Traitement de plantes au moyen d'acide salicylique et d'amines organiques

Info

Publication number
EP1100330A1
EP1100330A1 EP99934147A EP99934147A EP1100330A1 EP 1100330 A1 EP1100330 A1 EP 1100330A1 EP 99934147 A EP99934147 A EP 99934147A EP 99934147 A EP99934147 A EP 99934147A EP 1100330 A1 EP1100330 A1 EP 1100330A1
Authority
EP
European Patent Office
Prior art keywords
plant
nitrogen
acid
treated
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99934147A
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German (de)
English (en)
Other versions
EP1100330A4 (fr
Inventor
Frank W. Dean
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Stoller Enterprises Inc
Original Assignee
Stoller Enterprises Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Stoller Enterprises Inc filed Critical Stoller Enterprises Inc
Publication of EP1100330A1 publication Critical patent/EP1100330A1/fr
Publication of EP1100330A4 publication Critical patent/EP1100330A4/fr
Withdrawn legal-status Critical Current

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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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • 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

Definitions

  • the present invention generally relates to methods for improving disease resistance in plants without adversely affecting the plant growth. More specifically, the present invention is directed to methods for achieving such results by treating the plant tissue with an ortho- substituted benzoic acid and an organic amine.
  • Agricultural pesticides are used to control unwanted fungal, viral, and bacterial populations. These compounds have allowed the producer to manage disease pressure. Although, these traditional chemical applications have been valuable in the past it is unlikely that the producer will be able to use them at the same rate into the future. Therefore, improved methods for controlling disease by stimulating the plant's natural processes are desirable. For some years it has been known that plants have the ability to produce pathogenese proteins. Once these proteins are expressed plants may have the capacity to protect themselves from pathogenic insults. The efforts of individuals, chemical producers, and academic institutions are now concentrated on producing genetically manipulated species that either repress or express these enzymes or their perceived precursors. Innumerable compounds have been documented as inducers of the pathogenese proteins. However, because the compounds applied separately induce a given set or class of enzymes they have not been found to be efficacious in preventing infection in field hosts.
  • An inoculation with an array of elicitors would induce the expression of recessive enzymes of two or more classes. These enzymes would enable the treated plant to defend itself against pathogens.
  • Plants are continually under attack from pathogenic microorganisms.
  • the pathogenic insults from the exposure to fungal, viral, and bacterial assaults are frequently confined to the area of attack. These insults often cause lesions as the cell dies.
  • the cell death is part of a hypersensitive reaction (HR) to the pathogen.
  • HR hypersensitive reaction
  • This reaction acts as an inoculant for the lesion forming pathogen, and also, as an inoculant for unrelated pathogens.
  • This inoculation provides a systemic acquired resistance (SAR).
  • SAR systemic acquired resistance
  • the pathogenese proteins are chitinese enzymes
  • Class I catalytic activity, cystine rich (protein spacer between amino and carboxyl ends) - ethylene induced.
  • Auxins have been shown to induce expression of ethylene at very low concentrations when applied. They are also useful for the inducement of chitinase. Auxins have also been shown to induce a class of pathogenese proteins. Sugars have also been shown to induce ethylene biosynthesis.
  • Systemic resistance is typically characterized by a reduction in lesion size.
  • the lesion response is a programmed cell death to isolate the pathogen and prevent further infection.
  • the pathogenese related proteins When the pathogenese related proteins are expressed prior to disease inoculation the pathogens can be isolated within the lesion in a shorter time period. It has been postulated that those substances that induce pathogenese related proteins would prime the plant for disease resistance, if applied prior to the insults.
  • the infection resistance is not the same for all cultivars or pathogens.
  • the lesion size for a given infection can be inversely correlated with the dose of the inducing chemical administered and, if application of a given set of inducers at a concentration great enough to induce production of an array of pathenogese related proteins, then the pathogen insult could be minimized to the extent that no signs of infection would be visible. That is to say, there would be no visible lesion formation.
  • auxins a class of plant hormones, have been shown to promote the production of the gas in plants at low concentrations, i.e., Auxins may be used to elicit pathogenese related proteins for plant defense. Because Auxins have been well studied and auxin structure activity relationships have been identified, synthetic compounds with auxin like biological characteristics are readily contrived. Naturally occurring Auxins typically have an indole core structure. The indole becomes biologically active with either auxin or anti-auxin like activity with molecule functionality substitution. With the use of resonance structures the structural similarities are easily seen.
  • benzothiadiazoles and their derivatives as biologically active materials may be actually mimicking Auxins.
  • the relationship between ethylene and Auxins has been well documented.
  • the promotion of pathogenese related proteins from exposure to ethylene is also well documented, e.g., the use of Auxins and other ethylene elicitors for the purpose of inducing an array of pathogenese related proteins is now documented.
  • Ethylene is also documented to be expressed from injury to a plant. If one were to compare pathogenese related protein production from known elicitor applications then the difference in those proteins induced would be from either concentration applied, compound applied, or compounds application method. Because the amount of pathogenese related enzymes expressed is roughly proportional to the amount of inducer applied and because lesion size is proportional to the amount of pathogenese related protein produced, the amount of an inducement elicitor applied should maximize the promotional properties of the inducement elicitor without causing harm. For salicylic acid an optimum concentration would be greater than 75mM.
  • Phenolics are plant growth inhibitors. Natural growth inhibitors (phenolics) are found in growing and dormant plants, fruits and seeds. These compounds are thought to work in concert with the phytohormones to regulate the growth and development of organisms throughout their life cycle.
  • Salicylic acid application has also been found to inhibit ethylene biosynthesis, inhibit germination, block wound responses, interfere with membrane ion transport and absorption of roots, induce rapid membrane depolarization and collapse of the transmembrane electrochemical potential, reduce transpiration in leaves and epidermal strips, reverse ABA induced stomatal closure, affect leaf abscission, and affect growth inhibition. These responses will almost certainly cause a decrease in the potential yield of a crop.
  • United States Patent No. 5,654,414 to Ryals, et al states ". . .
  • the chimeric gene may need to be expressed at levels of 1% of the total protein or higher. This may be the case for fungal resistance due to increased proteinase inhibitor expression. In cases where the energy expended to produce high levels of foreign protein may result in a detriment to the plant whereas, expression of the gene only when desired, for instance when a fungal or insect infestation is imminent, would result in reduced drain on energy, and therefor yield.
  • salicylic acid has a Ka of 1 .05 X 10 "3 it would not generally exist as a protonated acid in the xylem, phloem or cytoplasm; a conjugate base or ester would probably exist in such an environment.
  • weak bases specifically amines
  • for the neutralization of the weak acid would mimic the naturally occurring compounds as found in nature.
  • High concentrations of phenolics have been found in the presence of amines during flowering.
  • Substituted phenyl compounds have long been known to inhibit the growth in plants. Nonetheless, some phenolic acids are known to induce the production of proteins that provide the SAR.
  • the SAR acts as an immunity response that protects the plant against fungus, bacteria, and virus. This response is generally triggered from interactions between the plant and pathogen, i.e., viral, fungal, and bacterial agents.
  • the immune response is a systemic gene expression that requires phenolic accumulation.
  • the SAR generally lasts weeks to months.
  • the cuticle is soluble in alcohol or ketone.
  • hydroxyl, carbonyl, or ketal functional groups in combination with the chelated metal ions may aid in the cation permeability through the cuticle to the plant cell.
  • copper salts either applied to the leaf or soil, when present in the cell at 10 to 100 times the amount necessary for normal growth and development, may control pathogens. Because of the efficacy of chelated copper the amount of copper salt necessary at an application to the soil or the plant itself to raise the copper content in tissue analysis is lowered.
  • the present invention is directed to processes for improving pant resistance to disease without inhibiting plant growth. These processes are broadly directed at treating the plant with an ortho-substituted benzoic acid and nitrogen-containing compounds that is selected from the group consisting of the organic amines and compounds which will metabolize to an organic amine. These processes have been found to be further improved by simultaneously treating the plant with a chelated micronutrient metal. Finally, even more improvement has been observed where the plant is further treated with an ethylene inducing compound. Alternatively, it has been found that the benzoic acid and derivatives and nitrogen-containing compounds may be applied as an amine salts of the substituted benzoic acid. The acid, nitrogen containing compound, and optionally, chelated micronutrient metal and ethylene-inducing compounding, should be applied to the foliage of the plant as a solution flocked with a suitable carrier medium.
  • the nitrogen-containing compound is selected from the group consisting of the polyamines, tertiary amines, propylamines, and organic compounds which will metabolize to produce a propylamine.
  • Preferred compounds are the organic amines having the structure
  • R.,, R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen and alkyls and substituted alkyls having not more than three carbon atoms, provided that R ⁇ R 2 and R 3 are not all hydrogen. Most preferred are monoethanolamine, propylamines and dimethylaminopropylamine (DMAPA).
  • the preferred ortho-substituted benzoic acid is salicylic acid.
  • the chelated micronutrient metal preferably is selected from the group consisting of the alkaline earth metals, the transition metals and boron.
  • the ethylene- inducing compound of choice is indole-3-butyric acid.
  • the method of the present invention has been found to increase the resistance to disease exhibited by a variety of crop plants. Most significantly, this increased resistance was achieved without the deleterious effects which condemned prior attempts to employ salicylic acid to prevent or minimize disease in plants. This result has been achieved by simultaneous application of a nitrogen-containing compound, most preferably a tertiary amine or propylamine in accord with the present invention. Accordingly, the methods of the present invention have solved the problems which previously plagued attempts to capitalize on the benefits associated with the use of salicylic acid.
  • the present invention provides processes for improving plant resistance to disease without inhibiting plant growth.
  • the processes of the present invention overcome the problems which plagued prior attempts to employ salicylic acid and related acids and salts. For example, while it has been known that treatment of plants with salicylic acid can inhibit disease, the treatments, unfortunately, have also resulted in a significant stunting, and even death, of the plants. It has been impossible to previously take advantage of the beneficial results of salicylic acid treatment.
  • Applicant has discovered that when treatment with the acid is combined with a nitrogen-containing compound , preferably selected amines, the deleterious effects have been overcome and plant resistance to disease have been improved without any adverse effect on growth.
  • the present invention is broadly directed to a process for improving plant resistance to disease without inhibiting plant growth.
  • the present invention is directed to the treatment of plants with an ortho-substituted benzoic acid and a nitrogen-containing compound selected from the group consisting of the organic amines and compounds which will metabolize to an organic amine.
  • the most preferred ortho-substituted benzoic acid is salicylic acid.
  • the preferred nitrogen-containing compounds are selected from the group consisting of the polyamines, tertiary amines, propylamines and organic compounds which will metabolize to provide a propylamine.
  • a particularly preferred group of amines are those having the structure
  • R R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen and alkyls and substituted alkyls having not more than three carbon atoms, provided that R R 2 and R 3 are not all hydrogen.
  • Particularly preferred are monoethanolamine, propylamines and DMAPA and mixtures thereof.
  • the acid and amine may be applied as the amine salt of the acid.
  • Most preferred are the amine salts of salicylic acids.
  • a chelated micronutrient metal Preferably these metals are selected from the group consisting of the alkaline earth metals, the transition metals and boron. Exemplary cations include copper, zinc and mangenese.
  • inclusion of an ethylene-inducing compound in the treatment may be beneficial.
  • An example of such an ethylene-inducing compound is indole-3-butyric acid.
  • the ortho-substituted benzoic acid and nitrogen-containing compound, together with the optional chelated micronutrient metal and ethylene-inducing compound, should be applied to the foliage of the plant.
  • Preferred treatment includes foliar application of the solution of those compounds in a suitable carrier medium. While the most preferred carrier medium is water, fertilizer solutions and any agriculturally acceptable medium may be employed.
  • the ortho- substituted benzoic acid should be present in the treating solution in a concentration of not more than about 0.1 M, preferably in the range of about 0.0001 M to about 0.01 M. However, the nitrogen-containing compound may be present in significantly higher percentage, up to about 25 percent-by-weight.
  • a solution of chelated metal ions, neutralized with sodium hydroxide, consisting of 1.5 x 10 "2 M Cu (II), 1.5 x 10 "2 M Zn (II), 1.8 x 10 "2 M Mn (II), and a 3.8 x 10 3 M sodium salt of salicylic acid was applied to snap dragons. The plants were severely damaged by the application and death of some plants followed.
  • the metals were provided in a form of the oxides chelated with citric acid and monoethanolamine. This concentrated solution was diluted 50 to 1 with water. The concentration of components in the following solution was about 0.0015M amine salt of salicylic acid, 0.006M each copper (II) and zinc(ll) and 0.007M mangenese (II). Commercial available Auxin (indole-3-butyric acid) was added as an ethylene- inducing compound. The solution so prepared, together with a control of water, was applied to Gerber Daisy infected with powdery mildew. A single foliar application was found to prevent infection. Subsequent applications of the same solutions applied at two week intervals continued to prevent infection.
  • Example 3 In a field test covering approximately 700 acres of watermelon infected with anthracnois was treated with a solution in accord with the present invention together with control. A concentrated solution was prepared in accord with the description in Example 2. A final solution for application was prepared 19 to 1 dilution with water. The concentration of components in the final solution is about 0.0038M amine salt of salicylic acid, 0.015M each copper (II) and zinc (II) and .018M mangenese (II). Again, Auxin was added as an ethylene-inducing compound.
  • Celery was successfully treated in accord with the present invention by a similar solution.
  • a final solution containing salicylic acid, an amine, chelated micronutrient metals and an ethylene-inducing compound was prepared in accord with that described in Example 3. That solution was foliar applied to celery in a Florida field. Three applications were made during the growing season. While no disease was present, an increase in biomass and size was recorded at harvest. Control plants were treated with water. Using a sample of thirty treated and thirty controlled, biomass and size were recorded at harvest. Harvest mass of the controlled plants averaged 1.04kg per plant while those treated with the salicylic acid/amine solution averaged 1.32kg per plant. Height of the plants was also increased from an average of 61cm to 64cm. Thus, treatment in accord with the present invention, far from stunting or inhibiting plant growth, resulted in a 5 percent increase size, together with a 27 percent increase in biomass.
  • Corn was treated with a solution in accord with that prepared in Example 3 except that a 50:1 dilution with water was used. While disease was not present during the growing period, an increase in grain mass was recorded at harvest. Average yield per acre at harvest for controls (treated with water) was about 181.9 bushels per acre; average for the portion of the field treated in accord with the present invention was about 192.5 bushels per acre. In both cases nitrogen was applied at a rate of 100 pounds per acre.
  • Example 7 Red Oak Lettuce was successfully treated in accord with the present invention in an experiment conducted at the University of Queensland in Australia. A single spray at early seedling stage soon after planting prevented disease. Further, significant increases both diameter and height were observed.
  • Example 8 A treatment solution in accord with that described in Example 3 above was prepared and foliar applied to the plants at early seedling stage. Ten plants were treated with that solution while an additional ten plants were maintained as a control treated with water. Average plant diameter increased from 25.2cm to 27.7cm, an increase of about 10 percent. Similarly, average plant height increased from 14.8 to 16.7cm, an increase of about 13 percent. Thus, not only did treatment of growth in the present invention prevent disease, but surprisingly produced significant increase in yield.
  • Example 8 A treatment solution in accord with that described in Example 3 above was prepared and foliar applied to the plants at early seedling stage. Ten plants were treated with that solution while an additional ten plants were maintained as a control treated with water. Average plant diameter increased from 25.2cm to 27.7cm, an increase of about 10 percent. Similarly, average plant height increased from 14.8 to 16.7cm, an increase of about 13 percent. Thus, not only did treatment of growth in the present invention prevent disease, but surprisingly produced significant increase in yield.
  • Example 8
  • Another test using Green Oak lettuce was set up to measure disease and plant diameter.
  • a single application of the solution described in Example 7 was made at the early seedling stage soon after transplanting. Fifteen plants were treated with that solution while fifteen more were maintained as controls treated with water. Diameter was determined by measuring the extremities of the outer leaves. Disease ratings was made by removing a plant from its whole and examining the roots. Ratings were graded on a visual scale from 1 to 5; of the roots graded 1 with no sign of infection while root showing severe pythium damage were rated 5. Treatment in accord with the present invention increased average plant diameter from 18.93cm to 23.07cm, an increase of 22 percent.
  • Example 10 The example demonstrates the effect of salicylic acid in growth inhibition when used with other amines. The work was conducted at Texas A&M Crop
  • Example 6 The procedure of Example 6 was followed with the exception that no nitrogen was applied.
  • the test plants were soybeans. It was found that the average unit per acre at harvest for the control (treated with water) was 44.6 bushels per acre while the average field per acre for plants treated with the solution used in Example 6 was 49.4 bashels per acre. It is to be noted that in both cases of Example 6 and in this Example, the solution was applied as a 2% solution.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Soil Conditioners And Soil-Stabilizing Materials (AREA)
  • Fertilizers (AREA)

Abstract

L'invention concerne des procédés servant à améliorer la résistance de plantes à des maladies sans inhiber leur croissance. Ces procédés consistent à traiter la plante au moyen d'un acide benzoïque ortho-substitué, de préférence acide salicylique, et d'un composé contenant azote et sélectionné dans le groupe constitué par des amines organiques et des composés se métabolisant en une amine organique tels que, de préférence, des polyamines, des amines tertiaires, des propylamines et des composés organiques qui se métaboliseront afin de produire une propylamine. On peut traiter simultanément ces plantes au moyen d'un métal micronutritif chélaté sélectionné, de préférence, dans le groupe constitué par des métaux terreux alcalins, des métaux de transition et bore. On peut enfin traiter ces plantes au moyen d'un acide complexe induisant éthylène, de préférence acide indole-3-butyrique. Le mode d'application préféré s'exécute sur le feuillage de la plante au moyen d'une solution dans un véhicule approprié.
EP99934147A 1998-07-30 1999-07-20 Traitement de plantes au moyen d'acide salicylique et d'amines organiques Withdrawn EP1100330A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US12620298A 1998-07-30 1998-07-30
PCT/US1999/016365 WO2000005954A1 (fr) 1998-07-30 1999-07-20 Traitement de plantes au moyen d'acide salicylique et d'amines organiques
US126202 2002-04-19

Publications (2)

Publication Number Publication Date
EP1100330A1 true EP1100330A1 (fr) 2001-05-23
EP1100330A4 EP1100330A4 (fr) 2004-04-14

Family

ID=22423546

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99934147A Withdrawn EP1100330A4 (fr) 1998-07-30 1999-07-20 Traitement de plantes au moyen d'acide salicylique et d'amines organiques

Country Status (12)

Country Link
EP (1) EP1100330A4 (fr)
JP (1) JP4443048B2 (fr)
KR (1) KR100944136B1 (fr)
AR (1) AR023318A1 (fr)
AU (1) AU779398B2 (fr)
BR (1) BR9912559A (fr)
CA (1) CA2338503C (fr)
MX (1) MXPA01000794A (fr)
NZ (1) NZ510201A (fr)
PE (1) PE20001008A1 (fr)
TR (1) TR200100309T2 (fr)
WO (1) WO2000005954A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ503884A (en) * 2000-04-10 2002-12-20 Horticulture & Food Res Inst Treatment of fungus in trees by injection of salicylic acid
JP4925077B2 (ja) * 2001-08-27 2012-04-25 エーザイ生科研株式会社 植物の病害防除剤およびそれを用いた病害防除方法
US8252722B2 (en) * 2003-08-22 2012-08-28 Stoller Enterprises, Inc. Controlling plant pathogens and pests with applied or induced auxins
ITMI20040402A1 (it) 2004-03-03 2004-06-03 Isagro Spa Miscele e metodo per l'induzione di resistenza nella pianta
US8207091B2 (en) * 2004-03-02 2012-06-26 Stoller Enterprises, Inc. Methods for improving growth and crop productivity of plants by adjusting plant hormone levels, ratios and/or co-factors
BRPI0609389A2 (pt) 2005-03-22 2010-03-30 Repros Therapeutics Inc tablete, composição e respectivos usos
GB0520726D0 (en) 2005-10-12 2005-11-23 Plant Impact Plc Agricultural composition
UA96076C2 (en) 2007-10-16 2011-09-26 Репрос Терапьютикс Инк. Use of trans-clomiphene
UA113291C2 (xx) 2011-08-04 2017-01-10 Метаболіти транскломіфену і їх застосування
US9687458B2 (en) 2012-11-02 2017-06-27 Repros Therapeutics Inc. Trans-clomiphene for use in cancer therapy
US10542753B2 (en) * 2015-03-03 2020-01-28 Zelam Limited Compositions for improving budbreak and flowering
KR20230154923A (ko) * 2021-03-31 2023-11-09 로레알 새로운 방부제 시스템, 및 이를 포함하는 화장료 조성물
FR3125415B1 (fr) * 2021-07-22 2024-02-02 Oreal Nouveau système de conservation

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD214522A1 (de) * 1983-03-25 1984-10-17 Forschzent Bodenfruchtbarkeit Mittel zur erhoehung der wasserausnutzung landwirtschaftlicher kulturpflanzen
RU2111653C1 (ru) * 1996-12-26 1998-05-27 Всероссийский селекционно-технологический институт садоводства и питомниководства Питательная среда для укоренения растений in vitro

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD214522A1 (de) * 1983-03-25 1984-10-17 Forschzent Bodenfruchtbarkeit Mittel zur erhoehung der wasserausnutzung landwirtschaftlicher kulturpflanzen
RU2111653C1 (ru) * 1996-12-26 1998-05-27 Всероссийский селекционно-технологический институт садоводства и питомниководства Питательная среда для укоренения растений in vitro

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO0005954A1 *

Also Published As

Publication number Publication date
CA2338503C (fr) 2009-09-29
AR023318A1 (es) 2002-09-04
NZ510201A (en) 2002-10-25
KR100944136B1 (ko) 2010-02-24
PE20001008A1 (es) 2000-10-11
AU779398B2 (en) 2005-01-20
TR200100309T2 (tr) 2001-05-21
AU5004199A (en) 2000-02-21
JP2002521399A (ja) 2002-07-16
CA2338503A1 (fr) 2000-02-10
BR9912559A (pt) 2001-10-09
MXPA01000794A (es) 2002-04-08
JP4443048B2 (ja) 2010-03-31
KR20010079592A (ko) 2001-08-22
WO2000005954A1 (fr) 2000-02-10
EP1100330A4 (fr) 2004-04-14

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