AU675319B2 - Fluid concentrated formulations containing phosphated polyalkoxylated tristyrylphenol derivatives which are useful in particular in agrochemistry - Google Patents
Fluid concentrated formulations containing phosphated polyalkoxylated tristyrylphenol derivatives which are useful in particular in agrochemistry Download PDFInfo
- Publication number
- AU675319B2 AU675319B2 AU66046/94A AU6604694A AU675319B2 AU 675319 B2 AU675319 B2 AU 675319B2 AU 66046/94 A AU66046/94 A AU 66046/94A AU 6604694 A AU6604694 A AU 6604694A AU 675319 B2 AU675319 B2 AU 675319B2
- Authority
- AU
- Australia
- Prior art keywords
- phosphated
- units
- tristyrylphenol
- diluent
- salt
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims description 35
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical class C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 title claims description 24
- 238000009472 formulation Methods 0.000 title claims description 13
- 239000012530 fluid Substances 0.000 title claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 30
- 125000006353 oxyethylene group Chemical group 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- -1 oxypropylene units Chemical group 0.000 claims description 8
- 239000011149 active material Substances 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 5
- 239000004548 suspo-emulsion Substances 0.000 claims description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical group [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 4
- 239000003905 agrochemical Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000004546 suspension concentrate Substances 0.000 claims description 3
- 239000012190 activator Substances 0.000 claims description 2
- 239000005667 attractant Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 230000002070 germicidal effect Effects 0.000 claims description 2
- 230000012010 growth Effects 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 239000003750 molluscacide Substances 0.000 claims description 2
- 230000002013 molluscicidal effect Effects 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- 239000003223 protective agent Substances 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- 230000002940 repellent Effects 0.000 claims description 2
- 239000003128 rodenticide Substances 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 239000003643 water by type Substances 0.000 claims description 2
- 230000031902 chemoattractant activity Effects 0.000 claims 1
- 239000006260 foam Substances 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 14
- 235000011187 glycerol Nutrition 0.000 description 9
- 239000007787 solid Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 description 1
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- 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
- A01N25/30—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 characterised by the surfactants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
f I 1
AUSTRALIA
PATENTS ACT 1990 COMPLETE SPECIF I CATION FOR A STANDARD PATENT
ORIGINAL
:..Name of Applicant: Actual Inventors: Address for Service: je* 9 p AddrInvention Title:rvice: ooo.
*ppg Invention Title: p RHONE-POULENC GERONAZZO S.p.A.
Valerio BRAMATI and Antonio MARCHETTO SHELSTON WATERS 55 Clarence Street SYDNEY NSW 2000 "FLUID CONCENTRATED FORMULATIONS CONTAINING PHOSPHATED POLYALKOXYLATED TRISTYRYLPHENOL DERIVATIVES WHICH ARE USEFUL IN PARTICULAR IN
AGROCHEMISTRY"
p.
p p p.
P
p p pp The following statement is a full description of this invention, including the best method of performing it known to us:- -la- The subject of the present invention is the development of fluid formulations, which are stable with time, of phosphated polyalkoxylated tristyrylphenol derivatives.
Commercial formulations containing phosphated polyethoxylated tristyrylphenol salts currently available use, as corresponding vehicle, mainly monopropylene glycol.
For reasons of physicochemical stability, these liquid formulations cannot unfortunately exceed concentrations of approximately 40% by weight of tristyrylphenol derivatives.
At higher concentrations, a separation phenomenon is encountered which is harmful to the homogeneity of the formulation and which causes significant difficulties when it is So later used.
In relation to the abovementioned disadvantages, this limitation in concentration of course represents a significant handicap as regards logistics and it would be desirable on an industrial scale to be freed of it.
:i The present invention provides fluid composition which is stable with time and with temperature, comprising at least one phosphated polyalkoxylated tristyrylphenol or I 15 a salt thereof and a diluent, wherein the said diluent is glycerol and the concentration of the phosphated polyalkoxylated tristyrylphenol or salt thereof in the diluent is at least by weight.
Preferably the concentration of phosphated polyalkoxylated tristyrylphenol or salt thereof in the said diluent is in the order of 50 to 80% by weight, and most preferably in the order of 70% by weight.
Glycerol unexpectedly turns out to be an advantageous substitute for monopropylene glycol.
-2- Like the latter, it proves to be a good solvent for phosphated polyalkoxylated tristyrylphenol derivatives and for their salts and advantageously, in comparison with monopropylene glycol, leads to corresponding formulations which are markedly more concentrated and stable.
Whereas monopropylene glycol does not make it possible to achieve concentrations greater than 40%, glycerol leads efficiently to formulations enriched up to in active products.
a Of course, these enriched formulations additionally retain the required qualities, namely good fluidity and good stability with time and with temperature.
10 Phosphated polyalkoxylated tristyrylphenol derivatives is understood to cover, according to the invention, derivatives in which the alkoxyl units are preferably oxyethylene and/or oxypropylene units. The number of these units generally varies between 4 and 100 depending on the desired hydrophile/lipophile balance. The number of these units preferably varies between 5 and 40. It can in particular be an e a ethoxylated/propoxylated tristyrylphenol derivative having oxyethylene (OE) and/or oxypropylene (OP) units with an OE/OP ratio which can vary between 100/0 and 50/50.
Mention may in particular be made, as specific examples of this type of surface-active agents, of phosphated ethoxylated tristyrylphenols containing 16, 20, 25 or 40 OE units and those containing 25 OE OP units.
These compounds are preferably in the form of their salts and more particularly of their alkali metal and alkaline-earth metal salts, such as the K, Na, NH 4 Ca, Mg, Zn and the like.
Glycerol can be used as the sole solvent or mixed with other solvents usual for this type of .surface-active agents. Of course, it is clear that, in the second possibility, the propcirtion of glycerol must remain such that corresponding -ormulations are obtained which are fluid and stabilized'with time'aid with temperature. This adjustment is only a routine ee matter for anyone skilled in the art.
*99 Mention may be made, as solvent capable of being introduced into the claimed composition as a mixture with glycerols, of in particular: water, monopropylene glycol, monoethylene glycol, glycols such as diethylene glycol, alcohols such as isobutanol and cyclohexanol, or alternatively N-methylpyrrolidine. It is understood that this list of solvents capable of being combined with glycerol is in no way limiting and that is within the capability of those skilled in the art to complete it.
Mention will very particuiarly be made, as preferred formulation according to the invention, of a composition containing 70% by weight of potassium salt of phosphated polyethoxylated tristyrylphenol, containing 16 OE units, in solution in glycerol.
Of course, the compositions according to the invention can additionally incorporate other conventional additives of antifreeze, dye, anti-foam or protecting agent, with respect to oxidation, U.V, radiation or pH variation, type.
1: The compositions according to the invention turn out to be particularly useful in 10 stabilizing active materials in formulations of dispersion, suspension or suspoemulsion type and the like, A dispersion is a general term referring to any two heterogeneous non miscible 0 °phases which are put together; it can be two non miscible liquids (emulsion), or it can be 0 a solid in a liquid (suspension).
0.
is A suspension results when a solid is dispersed in a liquid; this is also called a 000 colloidal sol.
A suspension concentrate is when there is a substantial amount of dispersed phase (solid) in the continuous (liquid) phase; in such a suspension, the interactions between the solid particles are important.
Finally, a suspoemulsion is a combination of a suspension and an emulsion; a suspoemulsion is thus constituted of a suspension of particles (solid) in the aqueous phase, along with the solid particles there are also oil droplets which are present in the aqueous phase (emulsion).
4a- These active materials are in particular agrochemical active materials such as, for example, fungicides, pesticides, insecticides, germicides, nematocides, molluscicides, rodenticides, attractants, repellents, herbicides or growth activators.
The examples presented below, without implied limitation of the present invention, will make it possible to demonstrate other advantages thereof.
EXAMPLE 1 The various compositions tested below .i4 oo** 6 re 4 9 9 prepared by addition of the required amount of potassium salt of phosphated ethoxylated tristyrylphenol, containing 16 OE units, in glycerol.
By way of comparison, the stability and the viscosity results shown below also give an account of behaviour of two control formulations of potassium salt of phosphated ethoxylated tristyrylphenol, containing 16 OE units, respectively as 40% and 60% by weight solutions in monopropylene glycol. In the case of the 40% by weight control solution, it is more specifically the compound marketed under the name Soprophor FLK 1 by Rh8ne-Poulenc Geronazzo.
The fluidity of each of the formulations was assessed by measuring its viscosity at two different o 15 temperatures; the viscosity measurements were carried out using a Brookfield L.V.T rheometer at revolutions/minute.
As regards the homogeneity of the said solutions, it was assessed visually at two separate' temperatures and at the end of a temperature cycle.
*9 This temperature cycle consists in causing the *9* temperature of the solution under test to swing between -5°C and 45°C with a periodicity of 24 hours and for a time of 1 month. Heating at 45 0 C is carried out using an autoclave.
The table shown below gives an account of the results observed after storing for two months.
6
TABLE
VISCOSITY STABILITY AT THE TmE2.
cycle ~.ft ft ft ft...
ft...
ft...
ft ft.
ft ft ft ft...
ft. ft ft..ft Control at 40% in 368 60 good good good
MPG
Control at 60% in s eparation separation separation composition 12307 1.325 good good good accoising to the invention at Composition 11220 1366 good good good according to the invention at These results confirm that fluid and homogeneous compositions containing high concentrations of phosphated rolyethoxylated tristyrylphenol salt arg obtained over a significant temperature range.
It is noticed that the control at 60% in monopropylene glycol leads to separation from room temperat~ure.
ft ft.
ft ft ft...
ft...
ft ft.
ft ft ft ft ft.
ft. ft ft ft ft ft ft.
Claims (8)
1. Fluid composition which is stable with time and with temperature, comprising at least one phosphated polyalkoxylated tristyrylphenol or a salt thereof and a diluent, wherein the said diluent is glycerol and the concentration of the phosphated polyalkoxylated tristyrylphenol or salt thereof in the diluent is at least 40% by weight.
2. Composition according to claim 1, wherein the concentration of phosphated polyalkoxylated tristyrylphenol or salt thereof in the said diluent is from 50 to 80% by weight and preferably approximately 70% by weight.
3. Composition according to claim 1 or 2, wherein the alkoxyl units of the se 10 phosphated polyalkoxylated tristyrylphenol or salt thereof are oxyethylene and/or oxyp'opylene units, with a number of units between 4 and 100. a
4. Composition according to claim 3, wherein the number of oxyethylene and/or oxypropylene units varies between 5 and Composition according to any one of the preceding claims, wherein the alkoxyl a 15 units of he phosphated polyalkoxylated tristyrylphenol or salt thereof are oxyethylene and/or oxypropylene units, according to a number of oxyethylene units/number of oxypropylene units ratio varying from 100/0 to 50/50.
6. Composition according to any one of the preceding claims, wherein the phosphated polyalkoxylated tristyrylphenol salt is a potassium salt of phosphated ethoxylated tristyrylphenol containing 1( ixyethylene units.
7. Composition according to any o.e of the preceding claims, wherein the composition additionally contains dyes, anti-foams and protecting agents with respect to oxidation, U.V. radiation or pH variations. -8-
8. Use of a composition forming the subject of any one of the preceding claims in the stabilization of active materials in formulations of suspension concentrate, emulsion or suspoemulsion type.
9. Use according to claim 8, wherein the active materials are agrochemical substances of fungicide, pesticide, insecticide, germicide, molluscicide, rodenticide, attractant, repellent, herbicide or growth activator type. A fluid composition substantially as herein described with reference to Example 1. DATED this 2nd Day of December, 1996 RHONE-POULENC GERONAZZO S.p.A. Attorney: PAUL G. HARRISON Fellow Institute of Patent Attorneys of Australia of SIIELSTON WATERS S S S S fOi f 9 ABSTRACT Fluid compositions which are stable with time and with temperature, consisting of at least one phosphated polyalkoxylated tristyrylphenol derivative and of a diluent, characterized in that the said diluent is glycerol and in that the phosphated polyalkoxylated tristyrylphenol concentration in the said diluent is at least 40% by weight. It can be used for stabilizing agrochemical good 10 active materials in formulations of suspension concentrate, emulsion or suspoemulsion type. l** 1. 4) 9 teo a
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9308324A FR2707181B1 (en) | 1993-07-07 | 1993-07-07 | Concentrated fluid formulations of phosphated polyalkoxylated tristyrylphenol derivatives usable in particular in agrochemistry. |
| FR9308324 | 1993-07-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6604694A AU6604694A (en) | 1995-01-19 |
| AU675319B2 true AU675319B2 (en) | 1997-01-30 |
Family
ID=9449002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU66046/94A Ceased AU675319B2 (en) | 1993-07-07 | 1994-06-28 | Fluid concentrated formulations containing phosphated polyalkoxylated tristyrylphenol derivatives which are useful in particular in agrochemistry |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0633057A1 (en) |
| JP (1) | JP2652000B2 (en) |
| AU (1) | AU675319B2 (en) |
| BR (1) | BR9402645A (en) |
| CA (1) | CA2127485A1 (en) |
| FI (1) | FI943236A (en) |
| FR (1) | FR2707181B1 (en) |
| ZA (1) | ZA944668B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY118564A (en) | 1998-02-10 | 2004-12-31 | Syngenta Participations Ag | Pesticidal compositions |
| GB0209225D0 (en) | 2002-04-23 | 2002-06-05 | Reckitt Benckiser Inc | Improvements in or relating to organic compositions |
| DE102005030526A1 (en) * | 2005-06-30 | 2007-01-04 | Clariant Produkte (Deutschland) Gmbh | Arylglycerinether |
| TWI513404B (en) | 2009-05-08 | 2015-12-21 | Croda Inc | Surfactants in agrochemical formulations |
| ITVA20130029A1 (en) * | 2013-05-27 | 2014-11-28 | Lamberti Spa | HYDRO-SOLUBLE POLYMERS FOR AGROCHEMICAL FORMULATIONS |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3302648A1 (en) * | 1983-01-27 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | PLANT PROTECTION AGENT IN THE FORM OF MIXED DISPERSIONS |
| JPH0635361B2 (en) * | 1985-08-19 | 1994-05-11 | クミアイ化学工業株式会社 | Pesticide composition in suspension |
| JPH0747521B2 (en) * | 1985-08-26 | 1995-05-24 | 東ソー株式会社 | Aqueous suspension formulation and application method for flooded paddy field after rice planting |
| JPS62242601A (en) * | 1986-04-16 | 1987-10-23 | Toho Chem Ind Co Ltd | Oil-in-water type agrochemical suspension composition excellent in storage stability |
| DE3631558A1 (en) * | 1986-09-17 | 1988-03-31 | Hoechst Ag | NEW SUSPOEMULSIONS OF PLANT PROTECTION ACTIVE INGREDIENTS |
| FR2630926B1 (en) * | 1988-05-04 | 1991-04-26 | Rhone Poulenc Chimie | SURFACTANT COMPOSITIONS BASED ON PHOSPHORIC ESTERS OF POLY (PHENYL-1 ETHYL) POLYOXYALCOYLENE PHENOLS, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION FOR OBTAINING AQUEOUS DISPERSIONS OF ACTIVATED MATERIALS |
| EP0514769B1 (en) * | 1991-05-18 | 1996-09-11 | Hoechst Schering AgrEvo GmbH | New suspo-emulsions based on Fenoxaprop-ethyl |
-
1993
- 1993-07-07 FR FR9308324A patent/FR2707181B1/en not_active Expired - Fee Related
-
1994
- 1994-06-22 EP EP94401402A patent/EP0633057A1/en not_active Withdrawn
- 1994-06-28 AU AU66046/94A patent/AU675319B2/en not_active Ceased
- 1994-06-29 ZA ZA944668A patent/ZA944668B/en unknown
- 1994-07-06 CA CA002127485A patent/CA2127485A1/en not_active Abandoned
- 1994-07-06 JP JP6176194A patent/JP2652000B2/en not_active Expired - Lifetime
- 1994-07-06 FI FI943236A patent/FI943236A/en not_active Application Discontinuation
- 1994-07-06 BR BR9402645A patent/BR9402645A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2707181B1 (en) | 1995-08-18 |
| FI943236A (en) | 1995-01-08 |
| AU6604694A (en) | 1995-01-19 |
| CA2127485A1 (en) | 1995-01-08 |
| EP0633057A1 (en) | 1995-01-11 |
| JP2652000B2 (en) | 1997-09-10 |
| FI943236A0 (en) | 1994-07-06 |
| FR2707181A1 (en) | 1995-01-13 |
| JPH07145013A (en) | 1995-06-06 |
| ZA944668B (en) | 1995-02-17 |
| BR9402645A (en) | 1995-04-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1163191A (en) | Flowable pesticides | |
| US4904695A (en) | Insecticidal aqueous-based microemulsion compositions | |
| US4536506A (en) | Insecticidal and acaricidal combination containing a pyrethroid | |
| US3948636A (en) | Flowable aqueous composition of water-insoluble pesticide | |
| US4500348A (en) | Oil-in-water emulsions, and their use | |
| US3894149A (en) | Pesticidal Concentrates | |
| BG65394B1 (en) | Herbicidal emulsifiable concentrates | |
| US6355679B1 (en) | Preservative compositions based on iodopropynl- and formaldehyde donor compounds | |
| US4851438A (en) | Aqueous pyrethroid insecticidal formulations in polyvinyl chloride containers, and methods of producing such formulations that are stable | |
| EP0331474B1 (en) | Spray formulations | |
| MXPA97003588A (en) | Emulsifiable composition for insec control | |
| AU610009B2 (en) | Transparent emulsion of pyrethroidal insecticide with a surface active agent and polar solvent | |
| AU2009228512B2 (en) | Surfactant compositions | |
| AU675319B2 (en) | Fluid concentrated formulations containing phosphated polyalkoxylated tristyrylphenol derivatives which are useful in particular in agrochemistry | |
| JP2009509949A (en) | Pesticide formulation with risk of crystallization and process for its production | |
| US5385948A (en) | Alkoxyalkyl lactams as solvents for macro and microemulsions | |
| CA1138216A (en) | Herbicides based on pyridazones | |
| US4923897A (en) | Stable aqueous pyrethroid insecticidal formulations for containment in polyvinyl chloride containers | |
| JPH0570307A (en) | Weeding method and herbicide composition for use therein | |
| AU600847B2 (en) | Stabilised pesticidal composition | |
| CS195654B2 (en) | Herbicide | |
| Rathburn | Insecticide formulations–types and uses: a review | |
| GB2138681A (en) | Agricultural compositions, methods of preparing agricultural compositions, and methods of using agricultural compositions | |
| TW302268B (en) | ||
| EP0369612A1 (en) | Insecticidal compositions |