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WO1987004047A1 - Dispersions regulatrices de la croissance des plantes - Google Patents

Dispersions regulatrices de la croissance des plantes Download PDF

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Publication number
WO1987004047A1
WO1987004047A1 PCT/US1986/002636 US8602636W WO8704047A1 WO 1987004047 A1 WO1987004047 A1 WO 1987004047A1 US 8602636 W US8602636 W US 8602636W WO 8704047 A1 WO8704047 A1 WO 8704047A1
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WIPO (PCT)
Prior art keywords
percent
weight
surfactant
oil
twenty
Prior art date
Application number
PCT/US1986/002636
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English (en)
Inventor
William Joseph Kowite
Stephen Louis Oestreicher
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Union Carbide Corporation
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Filing date
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Application filed by Union Carbide Corporation filed Critical Union Carbide Corporation
Priority to BR8607066A priority Critical patent/BR8607066A/pt
Publication of WO1987004047A1 publication Critical patent/WO1987004047A1/fr

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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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

  • This invention relates to dispersions of plant growth regulating compounds. More particularly it relates to water and oil formulations containing 2-haloethyl phosphonic acid compounds which are stable for extended periods of time over a wide range of ambient temperatures.
  • the preferred and most widely used phosphoric acid plant growth regulator compound is 2-chloroethylphosphonic acid which is known by the generic name "ethephon".
  • Ethephon is normally stored in solution of relatively high concentration for reasons of convenience and to minimize degradation which begins to occur at pH levels above about pH 5.
  • concentrated form ethephon exhibits a pH of about 1.0.
  • the concentrated solution is customarily diluted prior to application to plants at concentrations which exhibit a pH of about 3.5. 2 ,
  • a particular problem which it is sought to overcome by this invention is the rapid evaporation of water from aqueous formulations of ethephon which sometimes occurs when aqueous formulations of ethephon are applied through ULV apparatus. Such evaporation is so rapid that in some instances only the dry active reaches the plant.
  • Formulations of aqueous solutions of agricultural chemicals in an oil base are known in the art. Preparation of these emulsions or dispersions is accomplished by mixing the desired oil, water, active ingredient and an emulsifier in appropriate amounts to achieve the desired formulation.
  • Such emulsion compositions are typically 30-80% by weight oil and 10-40% water.
  • the emulsifier is present in smaller amounts, seldom exceeding 15% by weight of the final composition and more often at concentrations of 4-10%.
  • This invention provides dispersions containing 2-haloethyl phosphonic acid plant growth regulators that are stable and particularly well suited for use with ULV apparatus. They are prepared by mixing an aqueous solution of the 2-haloethyl phosphonic acid plant growth regulator with an oil and a substantial amount of surfactant. In some compositions a co-surfactant is also present.
  • This invention provides a stable plant growth regulating composition which comprises a dispersion, having a Brookfield viscosity of less than 800 cps and containing micelles no larger than about 300 n , of:
  • phosphonic acid plant growth regulator includes not only 2-haloethyl phosphonic acid compounds such as ethephon but also all derivatives thereof which act as plant growth regulators.
  • the preferred phosphonic acid plant growth regulator is 2-chloroethyl phosphonic acid, generically known by the generic name "ethephon" .
  • Ethephon is available as an aqueous concentrate of five to ninety-five percent.
  • Preferred concentrates contain from about sixty to about eighty percent by weight of phosphonic acid plant growth regulator.
  • a "dispersion,” “colloid” and “emulsion” as used herein describe macroscopically homogeneous but microscopically heterogeneous mixtures of two or more finely divided phases (i.e., solid, liquid or gas).
  • the dispersions of this invention typically comprise liquid-liquid mixtures, one of the liquids being an aqueous solution of growth regulating compound, the other being an "oil”, i.e., a liquid substantially immiscible with water.
  • the term “liquid substantially immiscible with water” as used herein includes all liquids which, when mixed with water in the ratios described in this invention, will separate into two discrete phases after equilibration, absent agitation or presence of emulsifier.
  • Liquid-liquid dispersions consist of a first liquid, which forms the continuous phase in which micelles containing droplets of a second liquid, the discontinuous phase, are uniformly distributed.
  • micelle refers to a molecular aggregate in which each surfactant molecule contains functional groups that interact independently with the oil and with the water.
  • the functional group that interacts with the water is known as a hydrophile (i.e., water lover) or lipophobe (i.e., oil hater) while the group that bonds to the oil phase is designated a lipophile (i.e., oil lover) or hydrophobe (i.e., water hater).
  • the dispersion is an oil-in-water (O/W) emulsion.
  • O/W oil-in-water
  • W/O water-in-oil
  • the oil is the continuous phase and water the secondary phase.
  • the micelles in such invert emulsions are "invert micelles"; the hydrophilic component of the surfactant surrounds the aqueous center while the hydrophobic component interacts with the surrounding oil.
  • the formulations of this invention are microemulsions which have a low viscosity, and are thermodynamically and chemically stable.
  • the small micelle size preferably ranging from about 10 to about 200 run, produces a minimal amount of light scattering. Therefore most of the microemulsion ⁇ of this invention are transparent, absent incorporation of a reagent or additive that is colored.
  • the micelles of this formulation may be as large as about 300 n in diameter, which may cause light scattering and render the formulations translucent.
  • the formulations of this invention must have sufficiently low viscosities to permit spraying onto target plants by conventional spray apparatus, and preferably by ULV equipment.
  • a wide range of viscosities are useful depending upon the apparatus used. Brookfield viscosities of greater than 800 cps are considered too thick for any conventional spray applicators and if the formulation is to be used in ULV equipment the viscosity preferably should not exceed about 300 cps and more preferably should be less than 100 cps. (The viscosities referred to are measured at 25°C with a Brookfield Viscometer Model RVT using a number 4 spindle at 20 rpm. )
  • the concentration of phosphonic acid plant growth regulator compound used in the formulation of this invention preferably ranges from about ten percent (10%) to about fifty percent (50%) by weight, depending primarily upon the intended use of the formulation, particularly the plant to which it is applied and the specific plant growth response desired.
  • the continuous phase is an oil, i.e., liquid which is substantially immiscible with water, which is not a solvent for the active compounds employed, and which is stable at pH of the growth regulator.
  • the oil and water must be sufficiently immiscible, in the ratio of water to oil used in a particular dispersion, that two discrete microscopic phases in the formulation will survive for extended periods of time over a temperature range of from about -20°C to about +50°C in the presence of all the ingredients incorporated into the formulation.
  • the dispersion should remain intermixed for at least two years in a temperature range of from -10°C to +35°C.
  • the oil should not be soluble more than 1% by weight in water.
  • the selected oil must be stable in the acidic medium produced by the phosphonic acid compound, which may be as low as 0.5 pH.
  • the oil employed should also be essentially non-phytotoxic to the target plants at the applied concentration.
  • the oil should either be non-toxic or, if toxic, require a time to kill or injure the plant that exceeds the useful or remaining growing season of the plant.
  • the oil is preferably sufficiently non-evaporative so that sprayed droplets of formulation reach the target plants in liquid form. The vapor pressure of the oil used for ULV applications must therefore be considered.
  • oils useful in the formulations of this invention are aromatic hydrocarbons; extracts derived from natural sources; aliphatic hydrocarbons containing up to thirty carbon atoms, up to four non-adjacent double bonds, and up to four halogen, carboxyl or hydroxyl substituents (provided, of course, that the compound is a liquid immiscible with water). Mixtures of these oils can also be used. Especially preferred oils include mixtures of paraffins or isoparaffins; benzene or alkylbenzenes containing up to four C. to C.
  • alkyl substituents fatty acids containing from about twelve to about thirty carbon atoms, such as oleic acid and linoleic acid, and their triglyceride derivatives; and extracts derived from natural sources, e.g., tall oil, palm oil, cottonseed oil, linseed oil, soybean oil, peanut oil, castor oil and lanolin. These listings are merely illustrative. Any oil having the required physical properties can be used.
  • the amount of oil in a particular formulation is dependent upon a number of empirical characteristics of the ingredients in that formulation.
  • the oil is present in an amount relative to the amount of water such that the oil forms the continuous phase in the final formulation.
  • the oil should be present in an amount by weight that exceeds the amount of water.
  • weight percentages of from about twenty to about sixty percent of oil are useful.
  • the water should not exceed twenty percent by weight, although in some instances, higher values can be useful.
  • a composition containing a small amount (about 10%) growth regulator and a high amount of surfactant (about 30%) and a substantial amount of oil (about 35%) approximately 25% by weight water is required.
  • the amount of water will seldom exceed 15% by weight of the final formulation.
  • the hydrophobic surfactant must be chemically stable at the low pH conditions produced by the phosphonic acid plant growth regulator compound, especially the very low pH conditions produced by the preferred concentrated aqueous solutions of phosphonic acid plant growth regulators. Further, the surfactant must not raise the pH to a level that would lead to decomposition of the active compound. As a general rule any hydrophobic anionic, cationic or nonionic surfactant that does not raise the system pH can be used. Formulations using anionic or nonionic surfactants appear to offer better long term stability.
  • HLB hydrophilic-lipophilic balance
  • the surfactant be hydrophobic arises because of the nature of the oils that are most useful in the compositions of this invention.
  • the substituted and unsubstituted aliphatic and aromatic hydrocarbons and the extracts from natural sources are non-polar or only slightly polar materials.
  • a hydrophilic surfactant of high HLB i.e., approximately 14-17. It was discovered, however, that in the presence of ten to fifty percent 2-haloethyl phosphonic acid, such surfactants fail to produce stable microemulsions.
  • the difficulty can be overcome if a hydrophobic surfactant, i.e., a surfactant of HLB less than about 8, is used.
  • surfactants that can be used in the compositions of this invention are mono-substituted glycerol derivatives of fatty acids containing from about ten to about thirty carbon atoms, e.g., monostearates, monooleates and monolaurates; sugar-based fatty acid derivatives containing from about ten to about thirty carbon atoms in the fatty acid chain; acetylated glycerides of natural oils (i.e., liquids extracted from natural sources); and polyethoxylated alcohols or alkylphenols with branched or straight chain alkyl groups containing from about six to about thirty carbon atoms.
  • Ester, phosphate ester and phosphate acid analogues of many of these agents may also be useful.
  • Stable hydrophobic amine or amide derivatives may also prove effective.
  • the especially preferred surfactants are the anionic or nonionic polyethoxylated derivatives of alcohols and phenols containing from about eight to about thirty carbon atoms and less than twenty moles of ethylene oxide per mole of alcohol or phenol.
  • compositions of this invention require the use of substantial amounts of surfactant. While the optimum amount must be determined empirically according to the amount of growth regulator and the nature and amount of the oil to be used, weight percentages ranging from about ten to about forty percent are typical.
  • microemulsions of this invention are their toleration of changes in the formulation HLB. Formation of a stable dispersion usually requires a delicate balancing of oil, water and surfactant. This is particularly true for microemulsions. For example, if a highly polar liquid or a very hydrophilic surfactant (i.e., one having an HLB value of 17 or more) were added to a stable microemulsion of non-polar oil, water and surfactant, the dispersion would separate into phases, either immediately or after standing, because the thermodynamic balance had been destroyed.
  • a highly polar liquid or a very hydrophilic surfactant i.e., one having an HLB value of 17 or more
  • microemulsions containing 2-haloethyl phosphonic acid and a hydrophobic surfactant tolerate the addition of significant quantities of very hydrophilic anionic or nonionic surfactant without losing their thermodynamic stability.
  • An emulsion containing as little as ten to fifteen percent by weight hydrophobic surfactant will remain stable if as much as nine percent by weight very hydrophilic surfactant is added. This characteristic is of practical advantage in that apparatus used to apply the emulsion can be cleaned simply with water.
  • hydrophilic surfactant In the absence of the hydrophilic surfactant, emulsion residues resist water because the surfactant is so hydrophobic that when rinse water is introduced into the apparatus, the emulsion residue coalesces and the water-immiscible liquid adheres to the walls of the apparatus. Incorporation of hydrophilic surfactant into the emulsion permits the emulsion residue to mix with the water and be washed away.
  • the components can be added in any order . but must be mixed together with sufficient vigor • until the microemulsion forms, usually at ambient temperatures. Occasionally slight heating up to about 50°C may be required. If, however, the proper amounts of growth regulator, oil, water or surfactant are unknown, or if the particular ingredients interact so that no microemulsion forms after mixing, a co-surfactant may be added.
  • a "co-surfactant” is a low molecular weight non-ionizing organic compound which contains a polar functional group and which enhances the interaction of surfactant, water and oil.
  • the co-surfactant can be incorporated into the mixture at any time during the preparation. If, however, the proportions of oil to water in a particular formulation must be very delicately balanced, addition of the co-surfactant should be done after the growth regulator, water, surfactant and oil have been mixed into a macroemulsion. The macroemulsion should then be vigorously mixed while co-surfactant is titrated into it. Titration continues until the opaque macroemulsion becomes transparent or translucent. Should the macroemulsion be colored, then some indication for conversion of macroemulsion to microemulsion should be monitored; for example, there might be a color change or disappearance of cloudiness.
  • Typical co-surfactants are straight chain aliphatic alcohols containing from one to about six carbon atoms.
  • branched or straight chain C 1 ⁇ C, 5 mono or polyhydroxy alcohols are suitable; formulations containing t-butanol, Cg-C,. linear alcohols, ethylene gly ⁇ ol or propylene glycol have given especially stable microemulsions.
  • Urea and substituted ureas containing up to four C.-C- alkyl substituents, and dialkylformamides containing C,-C 3 alkyl groups are useful; urea and dimethylformamide have proved particularly beneficial.
  • Trialkylphosphates containing C.-C 6 straight or branched alkyl groups can be used; tributylphosphate is an effective co-surfactant.
  • the amount of co-surfactant for a particular formulation must be determined empirically. However, typical concentrations range from about five to about thirty percent. When a co-surfactant is used, the amount of surfactant required in a formulation is generally reduced by about five to ten percent relative to formulations with no co-surf ctant.
  • Example 1 A microemulsion was prepared by combining 3.6 g 70% aqueous 2-chloroethyl phosphonic acid, 3.6 ⁇ _ mixwure of arometic hydroc_.r cns (?r r? ic 150, Exxon), and 2 g nonionic ethoxylated linear alcohol surfactant (Alfonic 1412-40, Conoco) and blending until a transparent liquid formed.
  • the microemulsion was stable, chemically and thermodynamically, up to 50°C.
  • Example 2 A.microemulsion was prepared by combining 3 g mixture of isoparaffinic hydrocarbons (Isopar M, Exxon), 3.5 g nonionic ethoxylated linear alcohol surfactant (Alfonic 1412-40, Conoco) and 3.5 g 70% aqueous 2-chloroethyl phosphonic acid and blending until a transparent liquid formed.
  • the microemulsion was stable, chemically and thermodynamically, up to 50°C.
  • Example 3 A microemulsion was prepared by combining 3 g mixture of aromatic hydrocarbons (HAN, Exxon) , 3 g nonionic ethoxylated linear alcohol surfactant (Alfonic 1412-40, Conoco) and 2 g 70% aqueous 2-chloroethyl phosphonic acid and blending until a transparent liquid formed.
  • the microemulsion was stable, chemically and thermodynamically, up to 50°C.
  • Example 4 A microemulsion was prepared by combining 5.3 g mixture of isoparaffinic hydrocarbons (Isopar M, Exxon), 2.8 g nonionic ethoxylated linear alcohol surfactant (Alfonic 1412-40, Conoco) and 1.9 g 70% aqueous 2-chloroethyl phosphonic acid and blending until a transparent liquid formed.
  • the microemulsion was stable, chemically and thermodynamically, up to 50°C.
  • Example 5 A microemulsion was prepared by adding to 30 g tall oil (L5 grade, Westvaco), 10 g free acid of a complex organic phosphate ester anionic surfactant (Gafac RM-510, GAF) and 10 g linear Cg-C.. alcohol mixture (Neodol 91, Shell), mixing until dissolution was complete, stirring in 30 g 70% aqueous 2-chloroethyl phosphonic acid and adding this macroemulsion to an equal volume of water. The microemulsion showed poor stability, separating into two phases after several hours.
  • a complex organic phosphate ester anionic surfactant Gafac RM-510, GAF
  • 10 g linear Cg-C.. alcohol mixture Naeodol 91, Shell
  • Example 6 A microemulsion was prepared by combining 0.7 g urea, 4 g 70% aqueous solution of 2-chloroethyl phosphonic acid, 1 g organic phosphate ester anionic surfactant (Emphos CS-341, Witco) and 4 g tall oil (L5 grade, Westvaco) and shaking until a clear liquid formed.
  • the microemulsion was stable, chemically and thermodynamically, from -20°C to 50°C.
  • Example 7 A microemulsion was prepared by combining
  • a microemulsion was prepared by combining
  • microemulsion 5 g oleic acid, 2 g free acid of complex organic phosphate anionic surfactant (Gafac PE-510, GAF), 1 g urea and 5 g 70% aqueous 2-chloroethyl phosphonic acid and mixing until a clear liquid formed.
  • the microemulsion was stable, chemically and thermodynamically, up to 50°C.
  • Example 9 A microemulsion was prepared by combining 4 g tall oil (L5 special grade, Westvaco), 1 g organic phosphate ester anionic surfactant (Emphos CS-341, Witco), 1 g tributylphosphate and 6 g 70% aqueous 2-chloroethyl phosphonic acid and mixing until a transparent liquid formed.
  • the microemulsion was stable, chemically and thermodynamically, up to 50°C.
  • Example 10 A microemulsion was prepared by combining 4 g tall oil (L5A special grade, Westvaco), 1 g organic phosphate ester anionic surfactant (Emphos CS-341, Witco), 1 g t-butanol and 6 g 70% aqueous 2-chloroethyl phosphonic acid and mixing until a transparent liquid formed.
  • the microemulsion was stable, chemically and thermodynamically, up to 50°C.
  • Example 11 A microemulsion was prepared by combining 4.5 g mixture of aromatic hydrocarbons (Aromatic 150, Exxon), 1.1 g free acid of complex organic phosphate ester anionic (hydrophobic) surfactant (Gafac RM-410, GAF), 0.8 g polyethoxylated iior-ylphenol (nydrophilic) burfac ant (Ar ⁇ ox 95 ⁇ , Arjay) and 2.5 g 70% aqueous 2-chloroethyl phosphonic acid and mixing until a transparent liquid formed.
  • the microemulsion was stable, chemically and thermodynamically, up to 50 ⁇ C. Residues remaining in storage or application apparatus were easily washed away with a water rinse.
  • Example 12 A microemulsion was prepared by combining 2.5 g tridecyloxypoly (ethyleneoxy) ethanol nonionic (hydrophobic) surfactant (Emulphogene BC-420, GAF) , 1.8 g nonylphenoxypoly (ethyleneoxy) ethanol nonionic (hydrophilic) surfactant (Igepal C0-997, GAF), 0.5 g ethylene glycol, 3.4 g mixture of isoparaffinic hydrocarbons (Isopar M, Exxon) and 1.8 g 70% aqueous 2-chloroethyl phosphonic acid and mixing until a transparent liquid formed.
  • the microemulsion was stable, chemically and thermodynamically, up to 50 ⁇ C. Residues remaining in storage or application apparatus were easily washed away with a water rinse.
  • Example 13 A microemulsion was prepared by combining 2.5 g nonionic ethoxylated linear alcohol surfactant (Alfonic 1412-40, Conoco), 1 g methyl isoamyl ketone, 3 g 70% aqueous solution of 2-chloroethyl phosphonic acid and 3 g mixture of isoparaffinic hydrocarbons (Isopar M, Exxon) and mixing until a transparent liquid formed.
  • the microemulsion was stable chemically and thermodynamically, up to 50°C. Residues remaining in storage or application apparatus were easily washed away with a water rinse.
  • a microemulsion was prepared by combining 2.5 g tridecyloxypoly (ethyleneoxy) ethanol nonionic (hydrophobic) surfactant (E ulphogene BC-420, GAF), 1.5 g nonylphenoxypoly (ethyleneoxy) ethanol nonionic (hydrophilic) surfactant (Igepal CO-997, GAF) 0.5 g methyl isoamyl ketone, 2.5 g mixture of isoparaffinic hydrocarbons (Isopar M, Exxon) and 3 g 70% aqueous solution of 2-chloroethyl phosphonic acid and mixing until a transparent liquid formed.
  • the microemulsion was stable, chemically and thermodynamically up to 50 ⁇ C. Residues were easily washed from storage and application equipment with a water rinse.
  • compositions of this invention can be applied with ULV equipment in neat form or after dilution with an oil extracted from a natural source; cottonseed or soybean oil are very commonly used for this purpose.
  • the decision to dilute will depend upon the concentration of active in the microemulsion, the ease of applying the formulation in neat form and the concentration of active needed to induce the desired response in the plant. Coverages ranging from about 0.1 to as high as about 30 lbs a.i./A have been used, although the emulsions are customarily applied at rates ranging from 0.5 to 2 lb a.i./A.
  • T Q is the day of application
  • r ⁇ l is observation seven days later
  • T 2 is observation fourteen days later.
  • EXAMPLE A The formulation of example 2.was applied with ULV equipment by airplane under a clear sky with no wind at a temperature of 82°F to twenty rows of a field planted four and one half months earlier with Stoneville 825 cotton. Coverage of 2-chloroethyl phosphonic acid was l ib. a.i./A. Interior parts of the treated plot were monitored for % boll opening, density of green bolls and % defoliation over a two week period. Observations were compared to those obtained for six untreated rows and to a field on which an aqueous solution of 2-chloroethyl phosphonic acid was applied at 1 lb. a.i./A by conventional spray equipment. Results are summarized in Table I.
  • EXAMPLE B The formulation of example 4 was applied with ULV equipment by airplane under a clear sky with no wind at a temperature of 82 ⁇ F to twenty rows of a field planted four and one half months earlier with Stoneville 825 cotton. Coverage of 2-chloroethyl phosphonic acid was 0.5 lb. a.i./A. Interior parts of the treated plot were monitored for % boll opening, density of green bolls and % defoliation over a two week period. Observations were compared to those obtained for six untreated rows and to a field on which an aqueous solution of 2-chloroethyl phosphonic acid was applied at 1 lb a.i./A by conventional spray equipment. Results are summarized in Table I.
  • compositions of this invention are at least equally effective as known aqueous growth regulator formulations. They offer the added advantage of being applicable with the modern ULV equipment.
  • Example A and B are shown on Table I. Note that the microemulsion of Examples 2 and 4 produced enhanced results when compared with aqueous solution applied at the same rate.
  • the microemulsion compositions of the invention outperformed the aqueous solutions based on observations two weeks after application. Moreover, the inventive formulations induced comparable if not better results in just seven days than the aqueous solutions produced after fourteen days.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cultivation Of Plants (AREA)

Abstract

Des compositions contenant un régulateur aqueux de croissance des plantes à base d'acides phosphoniques dispersés dans de l'huile sont stables et particulièrement appropriées dans l'utilisation d'appareils de pulvérisation à volume ultra-faible.
PCT/US1986/002636 1985-12-30 1986-12-10 Dispersions regulatrices de la croissance des plantes WO1987004047A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
BR8607066A BR8607066A (pt) 1985-12-30 1986-12-10 Dispersoes de reguladores do crescimento de plantas

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81489885A 1985-12-30 1985-12-30
US814,898 1985-12-30

Publications (1)

Publication Number Publication Date
WO1987004047A1 true WO1987004047A1 (fr) 1987-07-16

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PCT/US1986/002636 WO1987004047A1 (fr) 1985-12-30 1986-12-10 Dispersions regulatrices de la croissance des plantes

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CN (1) CN86108939A (fr)
AU (2) AU6890287A (fr)
BR (1) BR8607066A (fr)
CA (1) CA1282977C (fr)
EG (1) EG17951A (fr)
GB (1) GB2194226B (fr)
TR (1) TR22763A (fr)
WO (1) WO1987004047A1 (fr)
ZA (1) ZA869743B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0976329A1 (fr) * 1998-07-31 2000-02-02 Hoechst Schering AgrEvo GmbH Suspension aqueuse concentrée contenant des thidiazuron et ethephon
WO2000018235A1 (fr) * 1998-09-29 2000-04-06 Aventis Cropscience S.A. Procede d'inhibition de la fleur de canne a sucre et nouvelle composition
WO2004054360A3 (fr) * 2002-12-17 2004-10-07 Bayer Cropscience Gmbh Concentres de microemulsion

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX372713B (es) * 2012-02-27 2020-04-16 Inst De Ecologia A C Uso de una composicón herbicida para el control de plantas parásitas.

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1320870A (en) * 1970-11-02 1973-06-20 Amchem Prod Plant growth regulating compositions
FR2312956A1 (fr) * 1975-06-06 1976-12-31 British Petroleum Co Composition pesticide et procede pour son application

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1320870A (en) * 1970-11-02 1973-06-20 Amchem Prod Plant growth regulating compositions
FR2312956A1 (fr) * 1975-06-06 1976-12-31 British Petroleum Co Composition pesticide et procede pour son application

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0976329A1 (fr) * 1998-07-31 2000-02-02 Hoechst Schering AgrEvo GmbH Suspension aqueuse concentrée contenant des thidiazuron et ethephon
WO2000018235A1 (fr) * 1998-09-29 2000-04-06 Aventis Cropscience S.A. Procede d'inhibition de la fleur de canne a sucre et nouvelle composition
WO2004054360A3 (fr) * 2002-12-17 2004-10-07 Bayer Cropscience Gmbh Concentres de microemulsion

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AU6890287A (en) 1987-07-28
ZA869743B (en) 1987-08-26
CN86108939A (zh) 1987-07-22
GB2194226A (en) 1988-03-02
EG17951A (en) 1991-08-30
GB2194226B (en) 1990-02-07
TR22763A (tr) 1988-06-21
BR8607066A (pt) 1988-02-23
GB8719970D0 (en) 1987-09-30
CA1282977C (fr) 1991-04-16
AU6848490A (en) 1991-03-14

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