AU597314B2 - New aqueous emulsions of plant protection agents - Google Patents

New aqueous emulsions of plant protection agents Download PDF

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Publication number
AU597314B2
AU597314B2 AU65821/86A AU6582186A AU597314B2 AU 597314 B2 AU597314 B2 AU 597314B2 AU 65821/86 A AU65821/86 A AU 65821/86A AU 6582186 A AU6582186 A AU 6582186A AU 597314 B2 AU597314 B2 AU 597314B2
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weight
agent
ethylene oxide
compounds
phosphorylated
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AU6582186A (en
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Konrad Albrecht
Rudolf Heinrich
Hans Schumacher
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Hoechst AG
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Hoechst AG
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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
    • 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
    • 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

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

Description

2
COMMONWEALTH
PATENTS ACT 1952-69 COMPLETE
SPECIFICATION
(ORIGINAL)
Class Int. Class Application Number: Lodged: Z'5 E4 Complete Specification Lodged: Accepted: Published: Priority: l ki inflcft c~jlI~jT wilendl11cflts nvidc folK sectioni 49 ,Illd is co-rrect u Printing.
lfeiated Art: Name of Applicant: *Ad~dress of Applicant Actual Inventor: -Adldrezss for Service: HOEC-HST AKTIENGESELLSCHAFT 45 Bruningstrasse, D-6230 Frankfurt/Main Federal Republic of Germany KONRAD ALBRECHT, RUDOI.F HEINRICH and HANS SCHUMACHER EDWD. WATERS SONS, 50 QUEEN STREET, MELBOURNE, AUSTRALIA, 3000.
Complete Specification for the invention entitled: NEW AQUEOUS EMULSIONS OF PLANT PROTECTION AGENTS The follo.4lng statement is a full description of this invention, including the best method of performing it known to us HOECHST AKTIENGESELLSCHAFT HOE 85/F 269 Dr.AU/ml New aqueous emulsions of plant protection agents It is known, and described in European Patent Application 47,396, to prepare concentrated emulsions, stable on storage, of herbicidally active phenoxyalkanecarboxylic acid esters, having an aqueous base, using ester-soluble emulsifiers and water-soluble dispersing agents. The ester-soluble emulsifiers used, if appropriate as a mixture with alkylarylsulfonates, are polyethylene glycol esters of fatty acids, polyethylene glycol ethers of fatty alcohols, of glycerides or of alkylphenols and also polyoxyethylene and polyoxyprop lene block polymers. The dispersing agents used are phosphated alkylarylpolyethy- 0 Lene oxides, the ammonium, sodium or potassium salts of phosphorylated polystyrylphenylpolyethylene oxide or Sethylene oxide condensates of fatty amines.
The amounts of oil-soluble emulsifiers added are between 1.01 and 11.1 parts by weight per 100 parts by weight of phenoxyalkanecarboxylic acid ester. The amounts of dispersing agent are 0.5 to 5 parts by weight per 100 parts by weight of aqueous solution. Anti-foaming agents based on long-chain alcotnols and silicones are added in order to avoid the formation of foam which takes place in this 25 operation.
S Attempts to extend the use of the water-soluble ammonium, sodium or potassium salts of phosphorylated alkylarylpolyethylene oxides mentioned above to other active compounds than those mentioned in European Patent Application 47,396 result in considerable technical problems in use.
In storage tests of over 3 months at 50 0 C, demixing phenomena which are reversible only to a limited extent occur in a number of preparations.
Similar problems are observed with the phosphorylated poiystyrylphenylpolyethylene oxides described in European -2- 2 Patent Application 33,291; in the same way it is only possible to obtain colloidal emulsions of limited heat stability using alkylaryl polyglycol ether compounds described in DE-A 3,111,934.
Furthermore, it is described in EP-A 118,759 that terminally monophosphorylated ethylene oxide/propylene oxide/ ethylene oxide block copolymers or salts thereof can be employed as dispersing agents in order to obtain aqueous pesticide formuLations.
It has now been found, surprisingly, that certain wetting and dispersing agents which are soluble in water and organic solvents can be used advantageously in comparison 15 with the water-soluble dispersing agents of the phosphory- S Lated alkyLaryLpoLyethylene oxide type described in EP-A 47,396 and in comparison with the terminally monophosphorylated ethylene oxide/propylene oxide/ethylene oxide block copolymers described in EP-A 118,759.
The present invention therefore relates to plant protection agents based on aqueous emulsions containing one or more active compounds, which comprise, as the dispersing agent, an ethylene oxide/propylene oxide/ethylene oxide block copolymer which is phosphorylated in the alphaposition and the omega-position or a salt thereof.
a Suitable salts are, in particular, the alkali metal, alkaline earth metal, ammonium, monoalkylammonium, dial- 3,0 kylammonium or trialkylammonium or monoalkanolammonium, dialkanolammonium or trialkanolammonium salts. These contain, in particular, 1 to 5 carbon atoms in the alkyl or alkanol moiety, respectively.
The preparations according to the invention are substantially free from organic solvents and inorganic salts.
They can therefore be handled without risk, especially in transport and storage. The viscosity of the finished preparation can be adjusted without problems to the desired j I pll P 3 value by varying the polyethylene glycol content, so that it is possible to dispense with the dispersing and thickening agents which are otherwise customary.
8-wtab6e Phosphorylated ethylene oxide/propylene oxide/ ethylene oxide block copolymers to be used in accordance with the invention are, in particular, those of the formula I and salts thereof: 0
I
(HO)2P-[0-(CH2-CH2-0)xH-(CH-CH2-0)
-(CH
2
-CH
2 -0)J 0 C z C CH 3 ,P(OH)m
[(HO)
2 P-o-(cH-H 2 )x H 2
-CH
2 -0 CH 2
-CH
2 -0)z
CH
3 (I) i~Ys~ "8 4 *1
A
1i I d 20 Preferably, x and T-Ahave the same meaning and represent, in particular, a number from 30 to 100; y denotes, in particular, a number from 20 to 100 and n is, in particular, 0. These block polymers can be employed in the form of mixtures. Their preparation is described in JP-A 25 7,247,982 or in DE-A 3,542,441.
The formulations according to the invention can also contain, in addition, anti-freezing agents. These include, for example: ethylene glycol, propylene glycol, butane- 30 diol, urea, glycerol, polyethylene glycols and polypropylene glycols. They can also contain further formulation auxiliaries, such as customary dispersing agents, emulsifiers, thickeners and especially for solid active compounds also minor constituents of organic solvents.
Active compounds which can be employed for these preparations are, in particular, those which, by virtue of their low melting point, can only be converted with difficulty Sor not at all into a finely disperse aqueous phase by in which x, y and z independently of one another denote a number from 2 to 200 and m and n denote 0, 1 or 2, it being necessary for the sum of n m to be 2.
I means of grinding devices, or those in the case of which the grinding process demands special safety precautions.
Suitable active compounds for plant protection agents which can be employed are herbicides, insecticides, acaricides, nematocides, pheromones or repellents, it being necessary for these to be soluble in water only to a slight extent or not at all. Solid active compounds should, however, have a good to very good solubility in one of the organic solvents mentioned below.
Examnles of suitable herbicidal active compounds are alkyl phenoxyphenoxypropionates or alkyl heteroaryLoxyphenoxypropionates, such as methyl a-4-(2 ,41-dichlorophenoxy)-phenoxypropionate [common name: diclofopmethyll ethyl 2-[4-(6-chloro- 2-benzothiazolyloxy)-phenoxy]-propionate or ethyL 2- ["4-(6-choro-2-benzoxazoyoxy)-phenoxy]-propionate [common name: fenoxapropethyl] dinitroaniline compounds, such as 2,6-dinitro-4-trifuoromethy-N,N-dipropylaniline [common name: trifLuralin] or 2,6-dinitro- 4-isopropyl-N,N-dipropyLaniline [common name: isopropalin] hydroxybenzonitriLe derivatives, such as 2,6dibromo-4-hydroxybenzonitrile octanoate or dinitrophenol compounds, such as 2-sec.-butyl-4,6-dinitrophenol [common name: dinoterb] The following are examples of suitable insecticides: 1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-en-2,3-yLene dildethyl suLfite [common name: endosulfan], 2-(1-methyln-propyl)-4,6-dinitrophenyl 2-methylcrotonate [common name: binapacryll, phosphoric acid esters, such as 0,0diethyl 0-1-phenyl-1H-1,2,4-triazol-3-yl phosphorothioate [common name: triazophosl or pyrethroids, such as cyano-3-phenoxybenzyL-(1R,3R)-3-(2,2-dibromovinyL) 2,2dimethylcyclopropanecarboxylate [common name: deltamethr in] Ethyl 2-diethoxythiophosphoryloxy-5-methyl-pyrazoLo[
I
-CC -~ICPII- I~ I1I~III pyrimidine-6-carboxylate [common name: pyrazophos] should be mentioned as an example of suitable fungicides, and the compounds (E)-8-(E)-10-dodecadienol or (Z)-7,8-epoxy- 2-methyloctadecane should be mentioned as pheromones, and dimethyl phthalate should be mentioned as an example of repellents.
With the exception of the compounds and the abovementioned herbicides and the insecticides and the repellent are known from H. Martin, Pesticide Manual 6th edition 1979. The herbicides B) and C) are describe in German Offenlegungsschrift 2,640,730, and the two pheromones in M. Beroza, Chem. Controlling Insect Behaviour, Academic Press, N.Y. 1970.
Customary dispersing agents which may be employed in particular cases are preferably lignosuLfonates, Na salts of dinaphthylmethanedisulfonic acids, the Na salt of a sulfonic acid formed from cresol, formaldehyde, Na sulfite and hydroxynaphthalenesulfonic acid, the Na salt of a sulfonic acid formed from m-cresol, formaldehyde and Na 4 sulfite, condensation products formed from arylsulfonic acids and formaldehyde-Na salts, triethanolamine salts of phosphorylated polystyrylphenylpolyethylene oxides, polyvinyl alcohol, calcium dodecylbenzenesulfonate and alkylnaphthalenesulfonates of varying alkyl chain length.
Suitable emutsifiers are nonionic, anionic or cationic S surface-active substances, mixtures of nonionic and anionic 30 components being used predominantly. Combinations of i nonionic and cationic surface-active agents can also be used, however. The emulsifiers which can be employed preferentially include calcium phenylsulfonate, ethoxylated nonylphenols, ethoxylated aliphatic alcohols, ethoxylated castor oil, polyglycol esters of fatty acids, propylene glycol/ethylene glycol block polymers and mixtures thereof.
Water-soluble polymers, such as, for example, polyvinyl 1 yl-..
6 alcohol, polyvinylpyrrolidone and cellulose derivatives, can be used as thickening agents.
Suitable organic solvents are any water-immiscible solvents, for example aromatic compounds, such as toluene, xylenes, 1/2 methyLnaphthyLene or dimethyLnaphthalenes, aliphatic compounds, such as paraffin oils or vegetable oils, alicyclic compounds, such as cyclohexane, alkanols, such as cyclohexanol or i-octyl alcohol, ethers, such as diethyl ether, ketones, such as cycLohexanone, 4-methylcyclohexanone or isophorone, or esters, such as ethyl acetate and tri-n-butyl phosphate.
The plant protection agents according to the invention F -e e-rQ\y contain, -in pa rticulJ 5-60% by weight of active com- Spound, 10-90% by weight, preferably 15-40% by weight, of water and 0.5-20% by weight, preferably 1-10% by weight, of a compound of the formula I or salts thereof, and customary additives, if appropriate 5 to 50% by weight of an anti-freezing agent and/or 1-10% by weight of a dispersing agent and/or 1-15% by weight of an emulsifier and/or 1-10% by weight of a thickener and/or 1 to 30% by weight of an organic solvent.
The invention also relates to a process for the preparation of the agents according to the invention. For this purpose, the abovementioned components are stirred or shaken, in the required amounts, at temperatures between 00 and 600C, preferably at room temperature, in a zone 30 of high turbulence until the desired stable emulsion has been formed; in the course of this the particle diameter is adjusted to, preferably, 1-15 pm.
In order to carry out the process in practice, the aqueous phase (carrier phase) is first prepared by stirring the diols or polyols and the dispersing agent into water.
After this the emusifier component is added to the active compound to be emulsified, and the mixture is \finely dispersed in the aqueous phase. In the case of ~ern~ 7 active compounds having a melting point of approx. 0 C and higher, it can be necessary to prepare concentrated solutions thereof in one or more of the abovementioned organic solvents and to disperse these solutions in the aqueous phase after adding emulsifiers and, if appropriate, stabilizers.
It is also possible, however, first to mix the dispersing agent into the active compound and then to disperse the mixture into the aqueous phase.
Dispersing can be effected by a stirring process or, if appropriate, also a shaking process, and is preferably continued until the organic phase corresponds to the 15 desired droplet size. A droplet diameter of 1-15 pm is advisable. The dispersing process is preferably carried out at room temperature, but can, however, also be carried out under cold conditions or at elevated temperatures.
St S 20 The following examples are intended to illustrate the present invention in greater detail.
Formulation examples Example 1 0 6 36% by weight of methyl 2-(4-(2',4'-dichlorophenoxy)phenoxy)-propionate are dissolved by stirring in 18% by o weight of xylene at 20-25 0 C, and 6% by weight of a polygly- 30 col fatty acid ester (containing 40 EO) are added. 2% by weight of the potassium salt of the phosphorylated ethylene oxide/propylene oxide/ethylene oxide block polymer of the abovementioned formula I, n 0 (containing 68% of ethylene oxide in the end product) are also dissolved in 28% by weight of water at room temperature, and 10% by weight of ethylene glycol are then added. The abovementioned organic phase is allowed to flow slowly into this aqueous phase, with vigorous stirring by means of a blade stirrer, and the resulting white emulsion is stirred for I II- ~I 8 approx. 15 minutes further. One sample is stored for 3 months at 500C; another is stored for the same period at -10 0 C. The preparation is stable both to cheiicals and in use.
Example 2 32.3% by weight of technical endosulfan are dissolved, with stirring, in 21% by weight of a mixture of aromatic compounds (boiling range 219 0 C-282 0 and 4% by weight of the diethanolamine salt of the phosphorylated ethylene oxide/propylene oxide/,thylene oxide block copolymer of the abovementioned formula I (containing 55% of ethylene oxide in the end product) are added. 8% by weight of glycerol are dissolved at room temperature in 34.7% by weight of water. The organic phase is allowed to flow slowly into this solution, with vigorous stirring, and the resulting beige-colored emulsion is stirred for approx. 15-20 minutes further.
The preparation is stable to chemicals and in use.
Example 3 by weight of ethyl methylpyrazolo[1,5a]pyrimidine-6-carboxylate (pyrazophos) are dissolved, with stirring and at 20-25 0 C, in 18% by weight of xylene, and 6% by weight of a polyglycol ester (containing 40 EO) are added. 4% by weight of the pota- S' sium salt of the phosphorylated ethylene oxide/propylene o '30 oxide/ethylene oxide block copolymer of the abovementioned formula I, n o (containing 50% of ethylene oxide in the end product), are also dissolved at room temperature in 32% by weight of water, and 10% by weight of ethylene glycol are then added. The abovementioned organic phase is allowed to flow slowly, with vigorous stirring by means of a paddle stirrer, into this aqueous phase, and the resulting white emulsion is stirred for approx. 15 minutes further. One sample is stored for 3 months at 50 0
C;
another is stored for the same period at -100C. The 9 preparation is stable both to chemicals and in use.
Example 4 6.0% by weight of a polyglycol fatty acid ester (36 EO), 3% by weight of the free acid of the phosphorylated ethy- Lene oxide/propylene oxide/ethylene oxide block copolymer r\ =-O of the abovementioned formula I,(having a total content of 40% of ethylene oxide) and 10% by weight of glycerol are dissolved in 49% by weight of water. 32.0% by weight of (E)-8-(E)-10-dodecadienol are then run in, with vigorous stirring. The resulting white emulsion is stirred for a further 15 to 20 minutes.
ft The preparation is stable to chemicals and in use.
Example 30.0% by weight of technical endosulfan are dissolved, with stirring, in 21% by weight of a mixture of aromatic compounds (boiling range 2190C-282 0 and 3% by weight of the free acid of the phosphorylated ethylene oxide/propylene oxide/ethylene oxide block copolymer of the abover\ o mentioned formula I (containing 55% of ethylene oxide in the end product) are added. 12% by weight of polyethylene glycol (MW 1,000) are dissolved at room temperature in 34.0% by weight of water. The organic phase is then run in slowly, with vigorous stirring, and the resulting beige-colored emulsion is stirred for approx. 15-20 minutes further.
The preparation is stable to chemicals and in use.
Example 6 by weight of ethyl 2-(4-(6-chlor-2-benzothiazolyloxy)phenoxypropanoate are dissolved in 36% by weight of xylene at 40-450C, with stirring, and 4% by weight of the potassium salt of the phosphorylated ethylene oxide/propylene '1 10 oxide/ethyLene oxide block copolymer of the formula I, n o, having a total content of 60% of ethylene oxide, and 2% by weight of the triethanolamine salt of a phosphorylated polystyrylphenylpolyethylene oxide and 4% by weight of calcium dodecyLbenzenesulfonate are added.
9% by weight of ethylene glycol are dissolved at room temperature in 25% by weight of water. The abovementioned organic phase is run into this aqueous solution, with vigorous stirring by means of a paddle stirrer, and the resulting white emulsion is stirred for approx. 15 minutes further at room temperature. A sample is stored for 3 months at 50 0 C. The preparation is stable to chemicals and in use.
Example 7 by weight of 2,6-dinitro-4-trifluoromethyl-N,N-dipropylaniline (trifluralin) are dissolved in 20% by weight of xylene at 20-25 0 C, with stirring, and 3% by weight of the triethanolamine salt of the phosphorylated ethylene oxide/propylene oxide/ethylene oxide block copolymer of n=o the formula I (containing 55% of ethylene oxide) and 2% by weight of the triethanolamine salt of a phosphorylated polystyryLphenyLpoLyethylene oxide and 3% by weight of a polyglycol fatty acid ester (36 EO) are added. 6% by weight of polypropylene glycol (molecular weight 500) are dissolved at room temperature in 31% by weight of water.
The organic phase is allowed to flow slowly into this 30 aqueous solution, with vigorous stirring, and the resulting yellow emulsion is stirred for approx. 20-25 minutes further, until the pale yellow color shade of the emulsion undergoes no further change. The preparation is stable in use and to chemicals even after storage at various temperatures.

Claims (5)

1. A plant protection agent based on aqueous emulsions containing one or more active compounds, which com- prises, as the dispersing agent, an ethylene oxide/ ek eo^ b\oC:\ <po\>-CtZc oe\To propylene oxide/ethylene oxide block copolymer\Wb h" phosphorylated in the alplha-position and in the omega-position, or a salt thereof.
2. An agent as clain.ed in claim 1, wherein the dispersing agent used is a block copolymer of the formula I 0 (HO)2 -[O-(CH 2 -CH 2 -(CH-CH2-0)y-(CH 2 0 CH P(OH) CH 3 (I) i: B :ii r r 9 .e -;I a Ca a a a S a in which x, y anr z independently of one another de- note a number from 2 to 200 and m and n denote 0, 1 or 2, it being necessary for the sum of n m to be 2.
3. An agent as claimed in one of claims 1 or 2, which comprises 60% by weight of active compound, 90% by weight of water, 20% by weight of a compound of the formula I and customary additives.
4. An agent as claimed in one or more of claims which comprises, in addition, one or more of ing additives: 50% by weight of anti-freezing agent, 1 10% by weight of dispersing agent, 1 15% by weight of emulsifier, 1 10% by weight of thickener or 1 30% by weiqht of organic solvent. 1 to 3, the follow- An agent as claimed in one or more of claims 1 to 4, which comprises, as the active compound, a herbicide -12 HOE 85/F 269 selected from the group consisting of alkyl phenoxyphenoxy- propionates or aL kyL heteroaryLoxyphenoxypropioflptes, dinitroanilime compounds, hydroxybenzonitriLe deriva- tives or dinitrophenyl compounds, or an insecticide selected from the group consisting of endosulfan, binap- acryl, phosphoric aci~ esters or pyrethroids, or a qz ox fungicide, &Aiha~yaohs or a pheromone or a repel Ient.
6. An agent as cLaimed in one or more of claims 1 to which comprises, as the active compound, a compound selected from the group consisting of diclofopm'ithyl, fenoxapropethyL, trifLuoraL in, isopropaL in, 2,6-di- bromo-4-hydroxybenzoni tri Le octanoate, dinoterb, endosuLfan, binapacryL, triazophos, deLtamethriri, pyrazophos, dimethyL phthaLate, (E)-8-(E)-1O-dodeca- dienoL or (Z)-7,8-epoxy-2-meth~yloctadecane. DATED this 2 7 Lh (lay of Novefllhor 1986. HOECHIST AKT I EINGLSVI,.LSCHAF'F EDWD. WATERS SONS P)ATE1-NTI ATTO RN EY S QUEEN STREET MEL.BOURNE. VI C. 3000.
AU65821/86A 1985-11-30 1986-11-28 New aqueous emulsions of plant protection agents Expired AU597314B2 (en)

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DE19853542439 DE3542439A1 (en) 1985-11-30 1985-11-30 NEW AQUEOUS PLANT PROTECTION EMULSIONS
DE3542439 1985-11-30

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PL (1) PL262649A1 (en)
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AU629914B2 (en) * 1989-02-17 1992-10-15 Roussel-Uclaf New concentrated aqueous emulsions, process for preparing them and their use in the field of pesticides

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DE3542440A1 (en) * 1985-11-30 1987-06-04 Hoechst Ag NEW WATER DISPERSIBLE GRANULES
DE3917959A1 (en) * 1989-06-02 1990-12-06 Hoechst Ag LIQUID HERBICIDES
NZ239522A (en) * 1990-09-04 1993-10-26 Chapman Chem Co Pesticidal compositions containing an amine salt of a phosphonic or orthophosphoric acid
US5674514A (en) * 1992-09-21 1997-10-07 Ciba-Geigy Corporation Storage stable pesticidal aqueous emulsions
KR100298014B1 (en) * 1992-11-18 2001-11-30 카흐홀즈 트라우델, 귀틀라인 파울 Oil in water
DE4343856A1 (en) * 1993-12-22 1995-06-29 Hoechst Ag Oil-in-water emulsions
DE4343857A1 (en) * 1993-12-22 1995-06-29 Hoechst Ag Oil-in-water emulsions
GB9609436D0 (en) * 1996-05-04 1996-07-10 Zeneca Ltd Composition and use

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU629914B2 (en) * 1989-02-17 1992-10-15 Roussel-Uclaf New concentrated aqueous emulsions, process for preparing them and their use in the field of pesticides

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ATE57061T1 (en) 1990-10-15
DK573486A (en) 1987-05-31
DK573486D0 (en) 1986-11-28
GR3001158T3 (en) 1992-06-30
DE3542439A1 (en) 1987-06-04
HUT43228A (en) 1987-10-28
JP2581682B2 (en) 1997-02-12
PL262649A1 (en) 1987-11-30
AU6582186A (en) 1987-06-04
SK416891A3 (en) 1994-06-08
EP0224846B1 (en) 1990-10-03
DK174127B1 (en) 2002-07-01
EP0224846A1 (en) 1987-06-10
JPS62132801A (en) 1987-06-16
DE3674734D1 (en) 1990-11-08
ZA869001B (en) 1987-07-29
HU202714B (en) 1991-04-29
CZ416891A3 (en) 1993-07-14
CA1285785C (en) 1991-07-09
AR243318A1 (en) 1993-08-31

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