WO1983003041A1 - Stimulateur de la croissance de vegetaux comprenant des ions metalliques, des acides et sels carboxyliques d'alkyle a chaine longue, et leurs derives - Google Patents

Stimulateur de la croissance de vegetaux comprenant des ions metalliques, des acides et sels carboxyliques d'alkyle a chaine longue, et leurs derives Download PDF

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Publication number
WO1983003041A1
WO1983003041A1 PCT/US1983/000288 US8300288W WO8303041A1 WO 1983003041 A1 WO1983003041 A1 WO 1983003041A1 US 8300288 W US8300288 W US 8300288W WO 8303041 A1 WO8303041 A1 WO 8303041A1
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plant growth
composition according
carbon atoms
composition
formulations
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PCT/US1983/000288
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English (en)
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Marketing Corporation Biochemical
Andrew J. Welebir
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Biochemical Marketing Corp
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Application filed by Biochemical Marketing Corp filed Critical Biochemical Marketing Corp
Priority to BR8306107A priority Critical patent/BR8306107A/pt
Priority to AU14736/83A priority patent/AU1473683A/en
Publication of WO1983003041A1 publication Critical patent/WO1983003041A1/fr
Priority to OA58149A priority patent/OA07578A/xx

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    • 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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • 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
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A01N37/04—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
    • 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
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/06—Aluminium; Calcium; Magnesium; Compounds thereof
    • 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • 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
    • A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/10—Animals; Substances produced thereby or obtained therefrom
    • A01N63/14—Insects

Definitions

  • the present invention relates to chemical compositions which, when applied to growing plant life or seeds thereof, are effective in the growth of said plant life. More particularly, the invention relates to chemical compositions containing long-chain carbo ⁇ ylic acids and salts and derivatives thereof in combination with metal ions which are useful in stimulating plant growth.
  • Patent 3,619,168 to Mecklenborg describes the herbicidal utility of long-chain acids and esters with chain lengths between four and twenty-two carbons.
  • U.S. Patent No, 3,620,712 to Conklin also describes carboxylic acids with chain lengths between six and twelve carbon atoms as herbicidal agents.
  • Others have described other long-chain acids and esters for similar herbicidal use, such as Darlington in U.S. Patent No. 2,117,856 and Stewart, et al., in U.S. Patent No. 2,603,560, the former describing compounds having carbon chain lengths of twelve or less, and the latter, chain lengths of one to fourteen carbons.
  • an object of the present invention to provide an inexpensive and effective means of stimulating the growth of plants and increasing the yield of crops in the field.
  • composition of the present invention includes at least one compound of the formula:
  • R or R' are unsaturated, it is desirable that there be 1 to 6 double bonds, preferably 1 to 3 double bonds and most preferably only 1 double bond. It is preferred that R and R' both be straight chain alkyl groups, however, compounds wherein R and/or R' are branched are also useful in accordance with the present invention.
  • the Compound (I) is a carboxylic acid, monobasic carboxylic acids are preferred. However, dibasic and polybasic acids show comparable activity to monobasic acids and the number of carboxyl groups attached to hydrocarbon chain influences activity to a lesser degree than the number of carbon-carbon double bonds in the straight chain of the carboxylic acid.
  • the compounds of the present invention are preferably of the formula: R-COOR' (I) or a salt thereof wherein R is a saturated long-chain alkyl group having 15 to 47 carbon atoms and R' is hydrogen or a saturated alkyl group having between 1 to 36 carbon atoms.
  • R' may be over 36 carbons in length, these compounds are considerably more expensive to produce than the shorter chain analogs.
  • 1-tetracosanyl tetracosanoate shows superior effects than tetracosanoic acid, and is also superior to 1-methyl tetracosanoate. While not intending to be bound to the mechanism whereby the invention achieves its remarkable results, the longer the chain contributed by the R' group, the better the hydrophobic bonding to a plant "receptor" may be.
  • carboxylic acids are useful in carrying out the present invention, such as anhydrides, carbohydrate esters and the like, thiocarboxylic acids and esters and salts thereof, cholesteryl esters or other steroidal esters, amides, triglycerides, and other related compounds Any compounds which may release the free carboxylic acid, or salts or derivatives thereof, in aqueous solution by the action of acids or bases or other means are also within the scope of the present inventoin. Salts of the carboxylic acids of the invention are also highly useful, and show a higher solubility in aqueous solution than the free acids or esters.
  • saturated acids of the formula (I) include CH 3 (CH 2 ) 16 COOH (Stearic acid), CH 3 (CH 2 ) 18 COOH (Eicosanoic acid), CH 3 (CH 2 ) 20 COOH (Docosanoic acid), CH 3 (CH 2 ) 22 COOH (Tetracosanoic acid), CH 3 (CH 2 ) 24 COOH (Hexacosanoic acid), CH 2 (CH 2 ) 26 COOH (Octacosanoic acid), and CH 3 (CH 2 ) 28 COOH (Triacontanoic acid).
  • eicosanoic acid, tetracosanoic acid and triacontanoic acid are preferred.
  • saturated esters of the formula (I) include CH 3 (CH 2 ) 28 COOCH 3 (Methyl tria contanoate), CH 3 (CH 2 ) 34 COOCH 3 (Methyl hexatriacontanoate), CH 3 (CH 2 ) 40 COOCH 3 (Methyl dotetracontanoate), CH 3 (CH 2 ) 46 COOCH 3 (Methyl octatetracontanoate), CH 3 (CH 2 ) 22 COO(CH 2 ) 23 CH 3 (Tetracosanyl tetracosanoate), and CH 3 (CH 2 ) 22 COO(CH 2 ) 29 CH 3 (Triacontanyl tetracosanoate).
  • Methyl triacontanoate, Tetracosanyl tetracosanoate and Triacontanyl tetracosanoate are preferred.
  • Examples of polybasic carboxylic acids include HOOC(CH 2 ) 16 COOH (1,18-octadecanedioic acid), HOOC(CH 2 ) 20 COOH (1,22-docosanedioic acid), HOOC tetracosanedioic acid) and HOOC(CH 2 ) 10 2 10 OO
  • salts of the compounds of the formula (I) include, but are not limited to, salts having the formula (II) wherein X is Ca +2 , Na +2 , K + , Mg +2 , La +3 , Mn +2 , Zn +2 , NH + 4 , anilinium, octadecyl ammonium, and the like wherein n is the valence of the cation.
  • the compounds of the invention are solubilized in an aqueous solution containing at least one metal ion having a valence of +2 or more
  • the compounds may be dispersed in aqueous solution by any method practiced in the art, including simple solubilization of the compound in the aqueous solution by stirring, heating, and the like, or may be first dissolved in an organic solvent which is subsequently dissolved in a relatively large amount of water, with or without the aid of a surfactant, and preferably in a surfactant-free medium.
  • the most preferred method of solubilizing the compounds of the present invention in aqueous solution comprises coating the carboxylic acids, or salts or derivatives thereof, or combinations thereof, on the dry salts of the metal ions by means of a solvent in which any of the compounds being used to coat the metal ion salts are soluble. Subsequent dilution in water affords a highly useful solution of the compounds of the invention with metal ions.
  • the weight ratio of said compound to said metal salt is in the range of 1:1 to 1:5,000,000,000, preferably 1:5 to 1:500,000,000, more preferably 1:100 to 1:50,000,000 and most preferably 1:1,000 to
  • composition of the present invention contains the compound of the formula (I) and the metal salt in an amount effective to stimulate plant growth.
  • the composition will usually contain the metal salt in an amount of 50 grams to 1000 grams per kilogram, preferably 250 grams to 1000 grams per kilogram, most preferably 500 grams to
  • the compound of the formula (I) will be preferably contained in an amount of O.l ⁇ g to lOg per kilogram, preferably 50ug to 5g per kilogram, most preferably I ⁇ g to lg per kilogram of the composition.
  • the composition may contain additional active ingredients which improve or do not substantially inhibit the plant growth stimulating effects of the composition of the present invention.
  • the composition may also contain various inert ingredients (liquid or solid) which are incorporated into the composition in varying amounts depending upon the mode of application to plant life.
  • one part by weight of a compound of the invention, or mixtures of more than one compound is diluted to a final solution with up to about 5,000,000,000 parts of water (by weight), preferably diluted with between about 4,000 to 2,000,000,000 parts of water, and more preferably with between about 40,000 and 200,000,000 parts of water.
  • the effective range of concentrations of the compounds of the invention in solution with metal ions may vary widely while achieving similar results in stimulating plant growth and the yield of crops in the field.
  • the compound is first dissolved in the organic solvent, with or without the application of heat.
  • the resulting solution is then added to water, which may contain the metal ions of the invention, or the metal ions may be added after the addition of the concentrate.
  • one part (by weight) of one or more of the carboxylic acids or derivatives thereof of the invention is dissolved in between about one to 5,000,000 part of polar organic solvent (if no surfactant is to be added, or relatively nonpolar solvent if a surfactant is to be added), preferably one or more of the said compounds of the invention is dissolved in between about 10,000 and 500,000 parts of polar solvent (by weight), and more preferably, 10,000 parts to about 160,000 parts of solvent may be used, and most preferably between about 10,000 and 80,000 parts of solvent may be used.
  • one part of one or more compounds of the invention may be dissolved in between about one and 10,000 parts of nonpolar solvent, preferably between about 10 parts and 1,000 parts of nonpolar solvent, and more preferably between about
  • Polar organic solvents which are useful in carrying out the present invention in order to aid in the solubility of the long-chain compounds of the invention include, but are not limited to, ketones, alcohols, water-soluble ethers, glycols, sulfoxides, organic carboxylic acids of relatively low molecular weight, amines, dipolar, aprotic solvents such as DMSO (dimethyl sulfoxide), DMF (dimethyl formamide), and
  • HMPA hexamethyl phosphoramide
  • Typical polar organic solvents include acetone, methyl ethyl ketone, diethy ketone, cyclohexanone, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, t-butanol, sec-butanol, ethylene glycol, propylene glycol, diethylene glycol, glyme, diglyme, dioxane, tetrahydrofuran, acetic acid, formic acid, propionic acid, lower aliphatic amines, and other similar solvents which show a solubility in water and in which the compounds of the Invention are also soluble at concentrations where the resulting concentrate is useful in stimulating plant growth and crop yields when diluted to a final volume in water.
  • Nonpolar organic solvents which may be employed to aid in the dispersion of the compounds of the invention with or without the aid of a surfactant include, but are not limited to, hydrocarbons, higher alcohols, aromatic hydrocarbons, water-insoluble ethers, esters, amines, halogenated hydrocarbons, and the like.
  • Typical nonpolar solvents include chloroform, methylene chloride, carbon tetrachloride, freons, benzene, toluene, xylenes, aniline, pentanols, hexanols, heptanols, octanols, other long-chain alcohols, pentane, hexane, heptane, other hydrocarbon solvents, both aliphatic and aromatic, alkenes, alkynes, higher aliphatic amines, ethyl acetate, amyl acetate, other lower esters, and other nonpolar compounds in which the compounds of the invention are soluble, and which further may be dispersed in water containing metal ions, or before said metal ions are added to the solution, either with or without the aid of surfactant addifives.
  • the invention in aqueous media include, but are not limited to, Tweens, long-chain alkyl sulfonates, Zonyl surfactants, alkyl sulfates, nonionic surfactants, anionic surfactants, cationic surfactants, and other surfactants known in the art which are useful for dispersion of essentially nonpolar solvents or compounds in aqueous media. If surfactants are employed, they may be added either prior to or after the addition of metal ions to the aqueous solution, or prior to or after the addition of the solution of the compounds of the invention in an organic solvent to the aqueous portion of the formulation.
  • the amount of surfactant used is preferably kept to a minimum, since complexation or precipitation of the metal ions may occur, thereby lowering the growth promoting effect, or causing additional metal ions to be added.
  • surfactants are used up to a concentration (volume/volume) of about 5%, with a concentration of between about 0.1 and 3% being preferred, and a concentration of between about 0.1 and 1% being most preferred.
  • Metal ions of the invention which, in combination with the long-chain carboxylic acids, and salts and derivatives thereof, produce the remarkable growth-stimulating effects, include any cation having a valence of +2 or more. While metal ions of lower valence produce a small effect, a higher valence is required for the full growth-stimulating effect.
  • Typical metal ions useful in carrying out the present invention include, but are not limited to, Ca +2 , Ba +2 , La +3 , Cd +2 , Pb +2 , Co +2 , Mn +2 , Ce +4 , Mg +2 , Zn +2 , Cu +2 , Fe +3 , Fe +2 , Ni +2 , and the like, however, only a limited number of metal ions are preferred due to their superior effect and relatively low toxicity.
  • Metal ions of higher toxicity, such as Pb +2 and Cd +2 are very useful, and may be used on plant life not utilized for food purposes.
  • Other metal ions, such as Sr +2 are especially useful, however, the most preferred metal ions are Ca +2 , La +3 , Mg +2 , and Mn +2 due to their low toxicities .
  • Ca +2 is inexpensive, and useful salts are exempt from tolerance requirements by the U.S. Environmental Protection Agency. While some of these metal ions are known to affect the response of plants to the known plant growth substances, these belong to the well-known Hofmeister series, and include Ca +2 , La +3 , Mg +2 , and Mn +2 . The activity observed with other polyvalent metal ions, however, indicates that the biological activity of these cations in the compositions of the present invention may not be related to the known effects of the Hofmeister series cations. While the precise mechanism remains unclear at present, the metal Ions of the present invention, together with the compounds of the invention, were found inactive when applied separately -- not in combination — under identical conditions of application.
  • the compounds of the invention are either (1) added to a solution of metal ions in water in a polar organic solvent, or (2) coated on the dry salts of the metal ions of the invention by use of a suitable solvent which is subsequently allowed to evaporate, with or without the use of heat.
  • a suitable solvent which is subsequently allowed to evaporate, with or without the use of heat.
  • Preferred metal ion concentrations in the final/composition which is applied to plant life are between 0.1 and 50 mM, with concentrations of between about 1 and 30 mM being more preferred. If a surfactant is part of the final formulation, higher metal ion concentrations may be required, and may extend up to about 1 molar.
  • other plant growth substances appear to alter the effects of the compounds of the invention, such as auxins, gibberellins cytokinins, abscisic acid, ethylene, together with salts and synthetic analogs thereof.
  • auxins in particular, are capable of extending the useful range of metal ion concentrations which stimulate plant growth in the compositions of the present invention.
  • auxins include all natural and synthetic auxins, with auxins such as indole-3- acetic acid (IAA) and naphthalene acetic acid (NAA) being among the preferred auxins.
  • IAA indole-3- acetic acid
  • NAA naphthalene acetic acid
  • These may be added to the solutions of the compounds of the invention, or to the aqueous solution which may contain the metal ions of the invention, with or without the addition of the compounds of the invention. Alternately, they may be coated on the salts of the metal ions by any method practiced in the art.
  • Water-soluble salts of the auxins, gibberellins (such as gibberellic acid and the like), and cytokinins (such as kinetin, benzyladenine, and the like) are especially useful.
  • gibberellins such as gibberellic acid and the like
  • cytokinins such as kinetin, benzyladenine, and the like
  • the preferred mode of applications of the compounds of the invention in solution with polyvalent metal ions is foliar spraying of the formulations as a fine mist onto the leaves of plant life.
  • activity has been observed using other means of application, such as seed soaks, and soil drenches. Seed soaks have the advantage of requiring a small volume of the compositions of the invention, while soil drenches require considerably larger quantities.
  • the preferred ratio of seed to solution of the compounds of the invention including metal ions in solution is at least 2 parts solution to 1 part of seed (volume/volume), and similar results are achieved at higher solution to seed ratios, extending to about 25 to 1 or more.
  • Soil drenches require a considerable quantity of solution, amounting to between about 1 ml per plant to 10 liters per plant, with 1 ml to 1 liter per plant being preferred, and 5" ml to 1 liter per plant being more preferre
  • larger plants require larger volumes of solution than smaller plants, and plants with deeper root systems likewise require more solution to be applied to the soil in which they are growing.
  • Combinations of soil drenches, seed soaks, and foliar application are also useful, and other modes of formulation or application, such as formations of coloidal suspensions of the compounds of the invention, an the like, applied as innoculants, use of the formulations as fertilizer additives or complements, and the like, are not considered to be beyond the scope of the present inventio
  • the formulations of the present invention are useful on plant life at all stages of development, with some plants responding better at relatively early stages as compared to other plants.
  • the preferred stage of development is at the stage where the plant bears between about two and seven true leaves (or sets of two leaves each in the case of dicots, or up to the fifth trifoliate stage on beans and soybeans), with the preferred stage between three and six true leaves.
  • the metal ions of the invention are any metal ions havin a valence of +2 or more, and those released from inorganic metal salts are preferred, however, any organic or inorganic salt or compound capable of releasing an effective concentration of the desired metal ions in aqueous solution may be, used.
  • Counter ions such as C1 , NO 3 , acetate, and the like, are of minimal importance, since these do not appear to influence the activity of the cations of the invention. Also, some complexed metal ions may be useful, as well as aquated metal ions.
  • Salts of the carboxylic acids of the present invention are very useful in carrying out the methods of plant growth stimulation of the invention, and show improved solubility over the free acids of the invention.
  • These salts may be any known in the art which show a solubility in the concentration range useful for the carboxylic acids of the invention..
  • the salts of alkali metals show preferred water solubility, however, since the compounds of the invention show solubility at the low concentrations which are useful, described further henceforth, other metal salts are also of valuable use, such as salts of the metal ions of the invention.
  • salts of carboxylic acids, or derivatives thereof may include a plurality of metal ions, and metal ions useful in carrying out the invention may be in the forms of salts, of a plurality of long-chain compounds of the invention.
  • Patent 4,333,758 to the present inventor since the use of formulations containing metal ions and 1- triacontanol is severely limited for use on field corn, with responses being observed only on a few cultivars at a low, narrow range of metal ion concentrations, viz., between about 1.00 and 1. . 25 mM.
  • the compositions of the present invention show positive results on all cultivars of field corn tested with a similar formulation containing metal ions in the concentrations described above.
  • Crops which respond favorably are included in the group comprising, although not limited to, field corn, popcorn, sweet corn, milo, sorghum, wheat, barley, oats, rice, rye, apples, crabapples, pears, quinces, avocados, papayas, blackberries, dewberries, loganberries, raspberries, blueberries, currants, gooseberries, huckleberries, cherries, plums, prunes, oranges, citrus citron, grapefruit, kumquats, lemons, limes, tangelos, tangerines, mangoes, persimmons, peaches, apricots, nectarines, beans, peas, soybeans, broccoli, brussels sprouts, cauliflower, kohlrabi, cantaloups, honeydew melons, muskmelons, pumpkins, watermelons, winter squash, carrots, garden
  • Chinese cabbage salsify tops, onions, garlic, leeks, shallots, potatoes, Jerusalem-artichokes, sweet potatoes, yams, spinach, beet tops, collards, dandelion, kale, mustard greens, parsley, Swiss chard.
  • the formulations of the present invention may also be useful in enhancing the growth and quality of trees, such as loblolly pines, Australian pines, Douglas fir, pine trees, oak trees, and other trees.
  • the formulations of the invention are similarly useful for use on ornamental plants, including any plant used indoors or outdoors for ornamental purposes, and may be expected to show some effect on the growth of fungi under appropriate conditions.
  • compounds of the invention which show mammalian activity or other activity in life forms may be expected to show improved activity when combined with the metal ions of the invention.
  • naturally-occurring products which contain active amounts of the compounds of the invention are highly useful when combined in the formulations with metal ions.
  • these include naturally-occurring waxes and oils and the like, including compounds of the invention, or mixtures thereof, which are obtainable from natural sources.
  • These usually include useful compounds such as the long-chain carboxylic acids of the invention, esters thereof, hydroxy acids, and the like, and include both saturated and unsaturated compounds.
  • the compounds may further be present as esters of other naturally-occurring compounds containing carboxyl groups or hydroxyl groups, such as auxins, gibberellins, sugars, etc.
  • Useful naturally-occurring compounds include, but are not limited to, candelilla wax, carnauba wax, Chinese insect wax, esparto wax, ghedda wax, Japan wax, peanut oil, olive oil, rice bran oil, shellac, sisal wax, soybean oil, beeswax, etc.
  • the preferred members of the foregoing comprise any naturally-occurring wax, oil, and the like, which contain compounds of the invention, or mixtures thereof, such as beeswax, esparto wax, and the like.
  • such naturally-occurring waxes are used in the formulations of the invention, and may be used in any manner in which the pure compounds of the invention are utilized.
  • concentrated forms of the formulations made by coating a relatively small quantity of the naturally-occurring wax, oil, or the like, or mixtures thereof, directly on a metal salt of the metal ions of the invention, by means of an appropriate solvent or other means, as described in the foregoing description.
  • Formulations of more purified forms of the compounds of the invention such as those contained in naturally-occurring plant products, and the like, in combination with specific concentration ranges of added metal Ions in aqueous solution, however, offer superior improvements and refinements,over any prior art found by the present inventor.
  • the surprising results obtained through use of the formulations of the present invention will become apparent to the skilled artisan in the following description of the invention.
  • seed obtained from crops sprayed with the formulations of the invention show improved quality and may be expected to show increases in crop yields obtained through the planting of said seed with or without further application of the formulations, and, indeed, additive increases may be observed from growing season to growing season.
  • Improved germination has been observed on seeds of crops which require longer germination time or grow slowly on germination, such as tomatoes, peppers, celery, lettuce, tobacco, and the like.
  • Fig. 1 is a graph showing a typical dose response curve for the compounds of the invention, illustrated for the response of field corn (cv. Pioneer 3780) to formulations of the invention containing 3 mM CaCl 2 and varying concentrations of l-triacontanoic acid.
  • Fig. 2 is a graph showing the optimum hydrocarbon chain lengths of compounds of the invention for use on tomatoes
  • FIG. 3 is a graph showing the response of field corn seedlings (cv. Pioneer 3535) to formulations of the invention containing beeswax (10 ⁇ g/liter) and Ca +2 (2 mM) at different stages of development.
  • R - COOR' wherein R is a long-chain alkyl group containing from 15 to 47 carbon atoms, and may contain between about 0 to 6 carbon-carbon double bonds, and be substituted by about
  • R' is a long-chain alkyl group having between about
  • a 5 mg quantity of l-triacontanoic acid was dissolved with heating in 50 mL of acetone.
  • the concentrate was subsequently added to a solution of metal ions in water, and was applied as a foliar spray to plant life.
  • a 5 mg quantity of a long-chain ester was dissolved in 50 mL of a ketone or alcohol solvent, with or without the application of heat.
  • the solution was added to an aqueous solution of metal ions and applied to plant life, or used a a seed soak or soil drench.
  • a 150 mg quantity of a long-chain or fatty ester was dissolved, in 100 mL of trichloroethylene, with or without the application of heat. An amount of the resulting solution was then added to a solution of metal ions, with or without the aid of a surfactant additive, and sprayed on the leaves of growing plant life.
  • a 50 mg quantity of l-tetracosanoic acid (or other long chain acid or ester) was dissolved in 50 mL of acetone or other solvent in which the compound was soluble, with or without the application of heat.
  • the concentrate was subsequently used to coat the salt of a metal ion of the invention, allowed to dry, and the salt then solubilized in water and applied to plant life,, or used as a seed soak or soil drench.
  • Weight ratios (compound: salt) are ⁇ 1:100.
  • a 150 mg quantity of a naturally-occurring wax was solubilized in 100 mL of trichloroethylene, with or without the addition of heat.
  • the solution was then utilized to coat salts of metal ions of the invention, which were then dissolved In water to form a formulation with the desired concentration of both components.
  • the solution was then applied as described under Formulation 6, hereinabove.
  • FORMULATION 8 A 150 mg quantity of a naturally-occurring wax or oil solubilized in 100 mL of a nonpolar solvent, such as trichloroethylene, chloroform, benzene, and the like, and the resultant solution was further dissolved to allow sufficient volume resulting therefrom to coat a quantity of a metal ion salt, or combination thereof, relatively larger than that described under Formulation 7 hereinabove.
  • the solvent used to further dilute the concentrated solution may be selected from groups of solvents which are either polar or nonpolar in nature.
  • the resulting treated salts of the metal ions of the invention are then diluted in water after evaporation of the solvent.
  • EXAMPLE I A 0.1 mL quantity of Formulation 1 was added to a solution of MgCl 2 , or other metal salt, at a metal ion concentration of 3 mM in water, stirred, and sprayed on the leaves of field corn seedlings.
  • EXAMPLE II A 0.1 mL quantity of Formulation 1 was added to a solution of MgCl 2 , or other metal salt, at a metal ion concentration of 3 mM in water, stirred, and sprayed on the leaves of field corn seedlings.
  • a 1.0 mL quantity of Formulation 1 was added to a solution of CaCl 2 , or other Ca +2 salt, in water at a concentration of
  • a 0.1 mL quantity of erucic acid was dissolved in a suitable solvent, and this was added to 200 mL of water containing metal ions at a concentration of between about 10 mM and 15 mM.
  • the resultant solution was then applied to the leaves of tomato seedlings, or may be used as a seed soak for tomato seeds.
  • Beeswax or esparto wax was dissolved in a nonpolar solvent, such as trichloroethylene or the like, according to Formulation 7.
  • a nonpolar solvent such as trichloroethylene or the like
  • the solution was subsequently coated evenly on about 80 kg of anhydrous CaCl 2 and allowed to dry.
  • EXAMPLE IX A 0.33 mL aliquot of the solution described in Formulation 7 was added to 109 g of technical grade (77%) CaCl 2 , and the mixture was dried. After dissolving the granular product in 10 U.S. gallons of water, the solution was sprayed at the rate of 10 gallons/acre on one-half acre in two applications. EXAMPLE X
  • the compounds of the invention were obtained from the following sources: straight-chain, saturated and unsaturated carboxylic acids up to thirty carbon atoms were purchased from Sigma Chemical Co., St. Louis, Mo. Long-chain esters were synthesized either by esterification x ⁇ rith ethereal diazomethane, or through the reaction of the acid chloride with an alcohol. Amides were prepared through the reaction of acid chlorides with aqueous ammonia. Carboxylic acids and esters with a carbon chain longer than thirty carbons were prepared in accordance with the methods disclosed in either U.S. Patent No. 4,167,641, or those described in the Ph.D.
  • Results obtained were found similar whether plants were grown under natural or artificial lighting (ca. 750 to 1000 ft-can) for many plants tested.
  • 26 oCday temperatures were maintained with night temperatures of about 17 oC.
  • Plants grown by natural lighting were grown at the same time of year as normal for that particular plant in the field.
  • applications were made at varying temperatures, indoor temperatures were adjusted accordingly, and plants grown outdoors were sprayed at varying times of the day when the desired temperatures were reached. Plants were sprayed at various stages of development with formulations of the present invention as described in the examples given hereinafter. In all cases, randomized complete block designs were used, with each treatment being replicated between about 4 to 6 times.
  • plants were generally harvested at least four days after treatment, including roots, and soil was removed therefrom by washing with water. Fresh weights were obtained for each plot, and plants were dried to constant weight in an oven at a temperature below 100o C. Water content values were obtained by subtraction of dry weights from fresh weights, however, dry weights were used as the true indication of growth increases of treated plots over control plots. In field trials, increases in marketable yield were determined, and observations were recorded regarding increases in number of fruit, size of grain, and the like. All data were analyzed statistically by standard analysis of variance methods widely practiced in the art, and using Duncan's Multiple Range Test (Biometrics, 11: 1 (1955)).
  • the preferred mixture of compounds used was purified beeswax, which is known to contain esters of straight chain monohydric alcohols with even-numbered carbon chains from C 2 4 to C 36 esterified with straight-chain acids also having even numbers of carbon atoms up to C 36 (some C 18 hydroxy acids). Also contained therein are hydrocarbons with straight carbon chains from C 21 to C 33 (inert), as described in Merck Index, 9: 1027 (1976). The long-chain esters are also found superior to the carboxylic acids, and the small amount of l-triacontanol constituent in the wax is also shown in the following detailed description to be inert in the formulations of the present invention containing beeswax.
  • a Well water was obtained from the Northern Virginia area. Applied the 7th day after germination, harvested 4 days thereafter.
  • awell water from the Northern Virginia area was used in all treatments (pH 7.7).
  • b Applied at 10 U.S. gallons per acre equivalent.
  • c Applied at 20 U.S. gallons per acre equivalent.
  • aweights are the sum of 4 plants per plot, averaged for 5 replications. bcis-15-Tetracosenoic acid. cSprayed at 20.5° C.
  • % aWeights are the sum of 4 plants per plot average!, replicated 5 times.
  • bCompound l-triacontanol, in accordance with U.S. Patent 4,333,758 to the present inventor.
  • cSeedlings were fertilized 1 day after spraying with a water- soluble 15-30-15 fertilizer (2.5 g/L, 50 mL per plot).
  • dSeedlings were fertilized before spraying with a water- soluble 15-30-15 fertilizer (2.5 g/L, 50 mL per plot). TABLE 17. Increases in the Dry Weight of Soybean Seedlings
  • the number of sets of leaves refers to the number of sets of
  • Weights are the sum of 8 plants per plot, replicated 5 times. Plants were sprayed at an equivalent application rate of 20 U.S. gallons/acre. Weights reported are averages/5 plots.
  • Treatments were made at an application rate equivalent to 20 U.S. gallons/acre.
  • % % a Weights are the average -of plants containing 20 plants each. bSoil drench using 50 mL of the formulation applied to the roots of the plants (per plot). c Increase reported over controls which were treated with 50 mL of 20 mM CaCl 2 solution per plot. Note: When plants were not subjected to drought conditions, normal water content increases were in the 7 to 10 % range.
  • Plants had 4 to 5 Sets of True Leaves, and
  • Formulations of the Invention (Formulation 1) at pH 9 to 9.5 and 22° to 26° C, Harvested 4 to 7 Days Thereafter.
  • Table 1 shows the results obtained in promoting the growth of field corn seedlings (cv. Pioneer 3780) using various formulations of the invention, and further demonstates how additional plant growth substances may be used to enlarge the effective range of metal ion concentrations which are effective in the compositions to stimulate corn growth.
  • additional plant growth substances may not be required in the formulations due to the broad range of effective concentrations of metal ions on field corn (between about 1.5 and 4 mM being preferred).
  • metal ions such as Cd +2
  • Cd +2 While some metal ions, such as Cd +2 , are somewhat more effective than others, their use may be expected to be more limited due to the relatively high toxicity, and the use of said metal ions may best be limited to plant life not used for food purposes and the like.
  • Table 3 shows the effectiveness of a broad range of compounds of the invention in combination with Ca +2 on field corn (cv. Pioneer 3780), ranging from 24 to 48 carbon atoms in chain lengths of the carboxylic acids or their esters. Also, the pH of the solution applied to the corn seedlings appears to have no influence on the results obtained, with similar increases in dry weight being observed for formulations at pH 9.3 and 5.2.
  • Tables 4 and 5 show additional data for field corn (cvs. Pioneer 3320 and 3382, respectively), and include the mixture of esters contained in beeswax.
  • Tables 4 and 5 show additional data for field corn (cvs. Pioneer 3320 and 3382, respectively), and include the mixture of esters contained in beeswax.
  • Formulations 6 & 7 of the invention are highly economical due to the low cost of both beeswax and technical grade CaCl 2
  • the CaCl 2 used is further known to contain about 77% CaCl 2 with the balance being other metal ion salts, some of which are those of the present invention.
  • Table 6 shows the effects of temperature on cv. Pioneer
  • Table 7 compares application rates of the formulations of the invention on cvs. Pioneer 3744 and 3535. The data therein indicate that lower application rates may be preferr over higher ones, thereby making application of the formulations of the invention even more economical. Pioneer 3535 responds relatively poorly than other cultivars tested, and this may be related to the rapid growth rate observed with this cultivar. However, Table 8 shows that the stage at which the cultivar is sprayed influences the results, and other cultivars may be expected to respond to a higher degree when sprayed at different stages. Table 9 shows the effects of the formulations on cv.
  • nervonic acid a 24 carbon unsaturated acid (cis-15-tetracosenoic acid) shows some effect which is similar to that observed under the same conditions when beeswax was applied in the formulations of the invention. It is interesting to note that this cultivar (T-1000) and other later maturing cultivars respond better at a relatively higher temperature than the cultivars mentioned hitherto. Since these cultivars require a longer time to approach a stage where spraying should be done, this may be of advantage since temperatures at which the cultivars should be sprayed would be higher at that point in the growing season, and further advantage may be presented thereby. Tables 12 and 13 show that formulations of the invention show compatibility with fertilizers and herbicides on cvs.
  • Table 14 compares the results observed using the compo sitions of the present invention containing beeswax and 1-triacontanyl tetracosanoate and those of the prior art (as described in U.S. Patent No. 4,333,758 to the present inventor, and related applications).
  • l-triacontanol which is also contained in beeswax in small quantities, is found to stimulate plant growth only at alkaline pH, as shown for cv. Pioneer 3535.
  • Table 14 shows that no growth stimulation is observed with metal ions alone in solution, and that the triacontanol formulation containing NAA is effective only at alkaline pH.
  • soybean seedlings respond well to formulations of the present invention at preferred metal ion concentrations between about 5 and 15 mM.
  • the present invention is distinguished from the prior art by the fact that soybean seedlings have been found to respond to formulations of triacontanol only when the soil in which they are grown has sufficiently high phosphate content.
  • the temperature at which soybeans are preferably sprayed or otherwise treated with formulations of the invention appears to be broader than that observed in the case of field corn seedlings. Similar results are found using other cultivars of soybeans, such as cv. Essex and the like.
  • soybeans respond preferably to straight-chain carboxylic acids or salts or derivatives thereof which have a relatively longer hydrocarbon chain length than other crops such as tomatoes, peas and the like, i.e., compounds having about
  • field corn appears to respond to a relatively longer hydrocarbon chain length in the formulations than tomatoes (see Fig. 2).
  • peas respond to formulations of the invention to a higher degree when the hydrocarbon chain length of the compounds contained therein is relatively short, i.e., 22 or 24 carbon atoms as compared to about 30 carbon atoms. Also the formulations of the present invention are found superior in stimulating the growth of pea cultivars which respond somewhat poorly to triacontanol formulations, such as cv. Sugar Snap (prior art), both in the greenhouse and in the field.
  • waxes, oils, and the like which contain a lower average molecular weight hydrocarbon chain, such as peanut oil (C 16 to C 24 ), jojoba oil (C 20 to C 22 ), and other such waxes and oils and the like which are obtained from plant and animal sources.
  • Other compounds within the scope of the present invention which show increases in the growth of peas and may be expected to to show increases in the growth of other plant life when used in accordance with the invention also include, but are not limited to, erucic acid, tribehenin, dibehenoyl phospha tidyl choline (or other acidic phospholipids), and the like, with lower responses being observed for compounds such as 4,7,10, 13 , 16, 19-docosahexaenoic acid, 2-hydroxydocosanoic acid, lecithin, etc.
  • EXAMPLE XIV TOMATOES Several cultivars of tomatoes were treated with the formulations of the present invention with similar increases in growth resulting therefrom.
  • the data for the two cultivars shown in Table 22 Indicate that tomatoes respond to formulations of the invention containing compounds of the formula R-COOR', wherein R is between about 16 and 36 carbon atoms in length, with a relatively shorter hydrocarbon chain length being preferred to that in the case of soybeans.
  • waxes, oils, and the like are useful in the formulations of the present invention, such as beeswax (C 24 to C 36 ), jojoba wax or oil (C 20 to C 22 ), olive oil (C 16 to C 20 ), rice bran oil (C 16 to C 18 ), soybean oil, and the like.
  • beeswax C 24 to C 36
  • jojoba wax or oil C 20 to C 22
  • olive oil C 16 to C 20
  • rice bran oil C 16 to C 18
  • soybean oil and the like.
  • human sebum may be expected to have an effect on plant life when combined in the formulations of the present invention, causing Increases in the growth of plant life.
  • compositions of the invention are highly effective in improving the quality of seed prior to planting, and this mode of application may be preferred for seed of various crops which require long periods of time to germinate and produce seedlings of suitable size for transplanting in the field, such as tomatoes, tobacco, celery, lettuce, wheat, rice, and the like. Subsequent application of the formulations as foliar sprays, soil drenches, and the like, may be expected to further improve the growth of plant life and yields of certain crops.
  • Table 22 shows that the optimum metal ion concentration in formulations used for wheat in these examples is about
  • Results in field trials may be expected to equal or exceed those observed in these short-term greenhouse trials, as described in the foregoing Specification.
  • the formulations of the present invention were found active in promoting the growth of sweet corn seedlings through application in accordance with the methods of the Invention.
  • the increases observed were found to about equal to those observed for field corn seedlings in greenhouse studies under the conditions used, however, the concentrations of metal ions of the invention required for a response was found to be somewhat higher than those used in the case of field corn.
  • Concentrations of metal ions in the formulations applied which may be considered optimum are between about 3 mM and 10 mM, with between about 7.5 mM and 10 mM being preferred for sweet corn (Table 26).
  • EXAMPLE XVII TOBACCO Tobacco seedlings were tested with formulations of the invention, with results shown in Table 28. Optimum concentrations of polyvalent metal ions useful on tobacco seedlings are of a broad range, with similar results being observed four days after foliar spraying with formulations containing between 5 mM and 15 mM Ca +2 . Metal ions outside this range also produce effective plant growth stimulation. Similar activity is noted with other tobacco cultivars, with the preferred stage of application being about one to three weeks after seedlings have been set in the field.
  • formulations of the present invention are best accomplished at temperatures of about 22° C or more, preferably between about 22° and 33° C, however, positive results may be observed which take a considerable amount of time to germinate and attain a size suitable for transplanting in the field, may be soaked in formulations of the present invention prior to planting in beds to aid in improving both germination and increasing the growth rate thereof.
  • EXAMPLE XVIII COTTON Cotton seedlings respond favorably to the formulations described in the present invention, with increases in growth found in greenhouse trials shown in Table 29.
  • the leaves of cotton seedlings are easily coated with aqueous solutions of the compositions of the invention without the aid of any surfactant additive, as are leaves of other dicots such as cowpeas and the like, when applied as foliar sprays, and improved responses are noted at temperatures preferably of 24° C and higher.
  • Both the carboxylic acids and esters thereof of the invention (or their salts), and particularly waxy esters cause significant growth increases measured in terms of dry weights and compared to control plots.
  • esters and particularly waxy esters, show slight differences in the responses observed using carboxylic acids and their salts. Increases in the heights of the seedlings were also noted, however, these were found to be about 5 to 15% in difference as compared to controls.
  • EXAMPLE XIX PEPPERS Pepper seedlings respond well to the various formulation of the present invention, with greenhouse trial results on cv. Early California Wonder being reported in Table 30. An unusual response to formulations containing diferent metal ion concentrations and different compounds of the invention is observed, with a somewhat different metal ion concentration being preferred for compounds of the invention having varying hydrocarbon chain lengths.
  • EXAMPLE XX LETTUCE Lettuce (cv. Buttercrunch) was treated with two formulations of the invention and allowed to mature prior to harvest, Table 32 shows the increases in marketable yield found using formulations of the invention containing beeswax and varying concentrations of Ca +2 . Lettuce appears to respond to metal ion concentrations over a broad range as in the case of tobacco, reported hereinabove.
  • Table 33 shows that the formulations of the present invention are effective in stimulating the growth of potatoes. Also indicated by the data therein contained is that potatoes respond at a preferred temperature at the time of application below about 24° C, with a temperature of about 21° C being more preferred. This finding is advantageous to the grower since potatoes are genreally grown in cool climates, and arelatively higher temperature at the time the formulations of the invention may be applied is less likely to occur at the time of application of the formulations. It is important to note that root crops which show an increase in the dry weight of foliage obtained therefrom, also show similar increases in the size and weight of the crop itself when treated with the formulations of the present invention. For this reason, the dry weight of foliage from potato seedings was used as an indication of growth to predict optimum formulations of the present invention useful in the field to produce increases in crop yield.
  • EXAMPLE XXIII GRASSES Grasses of economic value, such as alfalfa, bluegrass, and the like, respond to formulations of the invention as evidenced by increases in the dry weight of the harvested grasses compared to controls (Tables 35,.37, and 38). Some grasses exhibit a growth-stimulating response at a narrow range of growth stages, such as Kentucky bluegrass (Table 35) while alfalfa generally responds over a somewhat broader range of stages of development (e.g., 8 to 20 cm in height, Tables 37 and 38). Grasses harvested for use as forage and the like generally respond to applications of formulations of the invention before the first cutting, and increases are observed with a second harvest without further application of the formulations. EXAMPLE XXIV: VEGETABLES AND OTHER CROPS
  • compositions of the instant invention As a result of the remarkable effectiveness of the compositions of the instant invention, other effects on plant are possible through the use thereof, such as improved disease resistance and cold resistance of plant life, and effects of this type have been observed.
  • sweet which was found susceptible to disease and produced no marketable yield on control plots was found to produce normal yields when treated previously with the formulations of the invention, and other effects similar thereto are also obser vable through the application of the formulations of the invention.
  • the long-chain compounds of the invention may act as "coating agents" in minute quantities, which may subsequently aid plant life in the use of absorption of the metal ions of the invention as micronutrients, foliar fertilizer agents, and the like. While other mechanisms are possible, any precise mechanism remains unclear.
  • the impact of the use of the formulations of the present invention has a high potential in the increase of world food supply, as well as the economical increase of resources derived from plant life useful as energy sources, building materials, and the like. Many other uses, yet unrealized, may evolve from the use of plant life if the supply of plant life "resources were to become economically plentiful, said uses being possible through the use of the compositions disclosed in the present invention.
  • Application of the formulations is conveniently made by the methods herein described, and may be made by other methods practiced in the art, such as addition of the components of the formulations to irrigation systems, application of said components to plant life as side dressings to be further diluted with water and absorbed by the root systems of plant life, and the like.

Abstract

Des formulations stimulatrices de la croissance de végétaux comprennent un ou plus d'acides carboxyliques à chaîne longue ayant entre 14 et 48 atomes de carbone, et leurs sels, esters et dérivés, et au moins un ion métallique ayant une valence de +2 à +3. Les formulations de l'invention sont extrêmement utiles pour stimuler la croissance de la vie végétale et pour augmenter le rendement des récoltes sur pied, par vaporisation foliaire, par trempage des graines et arrosage abondant des sols.
PCT/US1983/000288 1982-03-03 1983-03-03 Stimulateur de la croissance de vegetaux comprenant des ions metalliques, des acides et sels carboxyliques d'alkyle a chaine longue, et leurs derives WO1983003041A1 (fr)

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BR8306107A BR8306107A (pt) 1982-03-03 1983-03-03 Estimuladores do crescimento da planta que contem ions de metal e acidos alquilcarboxilicos de cadeia longa e sais derivados do mesmo
AU14736/83A AU1473683A (en) 1982-03-03 1983-03-03 Plant growth stimulators comprising metal ions and long-chainalkyl carboxylic acids and salts and derivatives thereof
OA58149A OA07578A (fr) 1982-03-03 1983-11-01

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CH665088A5 (fr) * 1985-08-22 1988-04-29 Nestle Sa Procede de preparation d'une composition utilisable pour stimuler la croissance des plantes.
EP0407142A1 (fr) * 1989-07-03 1991-01-09 Frank Henry Parker Procédé pour favoriser la croissance de champignons
WO1991013045A1 (fr) * 1988-12-30 1991-09-05 Sofrechim Polyacides organiques derives d'acides humiques et leurs utilisations en agriculture
WO1991018508A1 (fr) * 1990-05-28 1991-12-12 Sostra S.R.L. Composition empechant les degats causes aux cultures par l'ozone et procede d'application
US5186731A (en) * 1990-03-06 1993-02-16 Parker Frank H Method and compositions for promoting mushroom growth
EP1151667A2 (fr) * 2000-04-28 2001-11-07 Kao Corporation Agent d'activation de plantes
EP1151668A2 (fr) * 2000-04-28 2001-11-07 Kao Corporation Agent d'activation de plantes
WO2002071842A1 (fr) * 2001-03-09 2002-09-19 Kao Corporation Procede d'amelioration de cultures
CN114903041A (zh) * 2022-06-20 2022-08-16 华中农业大学 一种种子处理剂、制备方法和种子处理方法及应用

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GB201106763D0 (en) * 2011-04-20 2011-06-01 Exosect Ltd Compositions for growth and vigour in cotton
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GB201106764D0 (en) * 2011-04-20 2011-06-01 Exosect Ltd Composition for seed growth and vigour in monocots
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GB201106762D0 (en) * 2011-04-20 2011-06-01 Exosect Ltd Compositions for growth and vigour from oilseeds

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CH665088A5 (fr) * 1985-08-22 1988-04-29 Nestle Sa Procede de preparation d'une composition utilisable pour stimuler la croissance des plantes.
WO1991013045A1 (fr) * 1988-12-30 1991-09-05 Sofrechim Polyacides organiques derives d'acides humiques et leurs utilisations en agriculture
EP0407142A1 (fr) * 1989-07-03 1991-01-09 Frank Henry Parker Procédé pour favoriser la croissance de champignons
US5186731A (en) * 1990-03-06 1993-02-16 Parker Frank H Method and compositions for promoting mushroom growth
WO1991018508A1 (fr) * 1990-05-28 1991-12-12 Sostra S.R.L. Composition empechant les degats causes aux cultures par l'ozone et procede d'application
EP1151667A3 (fr) * 2000-04-28 2003-01-29 Kao Corporation Agent d'activation de plantes
EP1151668A2 (fr) * 2000-04-28 2001-11-07 Kao Corporation Agent d'activation de plantes
EP1151667A2 (fr) * 2000-04-28 2001-11-07 Kao Corporation Agent d'activation de plantes
EP1151668A3 (fr) * 2000-04-28 2003-07-02 Kao Corporation Agent d'activation de plantes
US6849576B2 (en) 2000-04-28 2005-02-01 Kao Corporation Plant-activating agent
EP1570735A1 (fr) 2000-04-28 2005-09-07 Kao Corporation Agent d'activation de plantes
US7829500B2 (en) 2000-04-28 2010-11-09 Kao Corporation Plant-activating agent
WO2002071842A1 (fr) * 2001-03-09 2002-09-19 Kao Corporation Procede d'amelioration de cultures
EP1366663A1 (fr) * 2001-03-09 2003-12-03 Kao Corporation Procede d'amelioration de cultures
EP1366663A4 (fr) * 2001-03-09 2004-07-28 Kao Corp Procede d'amelioration de cultures
CN114903041A (zh) * 2022-06-20 2022-08-16 华中农业大学 一种种子处理剂、制备方法和种子处理方法及应用
CN114903041B (zh) * 2022-06-20 2023-08-15 华中农业大学 一种种子处理剂、制备方法和种子处理方法及应用

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NO834008L (no) 1983-11-03
GB2118158B (en) 1985-09-11
PT77107B (en) 1986-01-27
GB8305706D0 (en) 1983-04-07
PT77107A (en) 1983-08-01
EP0103644A1 (fr) 1984-03-28
GB2118158A (en) 1983-10-26
JPS59500319A (ja) 1984-03-01
EP0103644A4 (fr) 1984-07-26

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