US3342581A - Pesticidal wettable powder formulation - Google Patents

Pesticidal wettable powder formulation Download PDF

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US3342581A
US3342581A US281801A US28180163A US3342581A US 3342581 A US3342581 A US 3342581A US 281801 A US281801 A US 281801A US 28180163 A US28180163 A US 28180163A US 3342581 A US3342581 A US 3342581A
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powder
wetting
wettable powder
sodium
parts
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US281801A
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Fred E Woodward
Stefcik Andrew
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GAF Chemicals Corp
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General Aniline and Film Corp
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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
    • A01N25/12—Powders or granules
    • A01N25/14—Powders or granules wettable
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03—Organic sulfoxy compound containing

Definitions

  • This invention relates to wettable powders, and more particularly to wettable powders which are capable of being readily dispersed in Water to form relatively stable, low-foaming aqueous dispersions.
  • the invention also relates to a wetting agent excellently adapted for utilization in the preparation of readily dispersible wettable powder formulations.
  • supplemental agents having wetting, dispersing, and/0r suspending properties is widespread in the preparation of formulations containing water-insoluble powders, such as insecticides, herbicides, fungicides, nematocides, fertilizers, and other industrially employed powders, to render the powders dispersible in water.
  • water-insoluble powders such as insecticides, herbicides, fungicides, nematocides, fertilizers, and other industrially employed powders
  • the wettable powder formulations are fast wetting when dispersed in water and form suspensions having relatively high solids contents which are low foaming and do not exhibit tendencies toward sedimentation with age.
  • wettable poW- ders particularly pesticidal wettable powders
  • attempts have been made in the art to find supplemental wetting and dispersing agents which are capable of providing wettable powders having the desired characteristics.
  • alkyl sulfo esters i.e., esters of sodium isethionate and long chain fatty acids of the formula RCOOCH CH SO M and alkyl sulfo amides, i.e., substituted amides of sodium aminoethionate and long chain fatty acids of the formula R0 0l ICHzCH2S 03M wherein M is alkali metal, R is an aliphatic hydrocarbon radical of -22 carbon atoms and R is H or lower alkyl (1-6 carbon atoms) or cycloalkyl (3-8 carbon atoms), are commonly employed as wetting-dispersing agents in preparing pesticidal wettable powders.
  • the resulting powders are characterized by excellent Wetting and suspensibility properties, but undesirably form aqueous dispersions which are relatively high foaming. Consequently, suspensions formed from such powders are incapable of being used completely satisfactorily in many types of application equipment. Moreover, due to the formation of foam upon the use of a dispersion containing the powder, an appreciable portion of the powder is trapped therein with a corresponding reduction in the efiiciency of the particular treatment contemplated.
  • the present invention provides a wetting agent for utilization in preparing wettable powders, said wetting agent comprising 1) a surface-active substance of the formula wherein R is an acyclic hydrocarbon radical, said surface-active substance having an average of from about 10 to about 22 carbon atoms per molecule in R, M is an alkali metal, and X is selected from the group consisting of O- and N wherein R is selected from the group consisting of hydrogen, alkyl having from 1 to about 6 carbon atoms, and cycloalkyl having from 3 to about 8 carbon atoms; (2) from about 5 to about 50 parts by weight per parts of said surface-active substance of a nonionic surfactant; and (3) from 0 to about 50 parts by weight per 100 parts said surface-active substance of an acid material having an average of from about 12 to about 20 carbon atoms per molecule selected from the group consisting of rosin acids, fatty acids, alkali metal soaps of said acids, and mixtures thereof.
  • the present invention also provides a wettable powder formulation comprising (A) a water-insoluble powder,
  • the surface-active substance employed in the wetting agents and wettable powders of the invention includes a single compound corresponding to Formula 1, given hereinabove, wherein R has from about to about 22 carbon atoms, mixtures of such compounds, and mixtures of compounds corresponding to Formula I wherein R has from about 7 to about 24 carbon atoms and the average number of carbon atoms per molecule in the radical R is in the range of from 10 to about 22.
  • the radical R may be straight or branched-chain in structure and saturated or unsaturated in nature.
  • R may be n-heptyl, n-nonyl, n-decyl, n-undecyl, i-dodecyl, n-tridecyl, i-tetradecyl, n-heptadecyl, n-tridecenyl, n-tetradecenyl, n-heptadecenyl, eicosyl, n-heneicosyl, decosyl, tetr-acosyl, and the like.
  • Such radicals are obtained by the use of acids RCO H, in preparing the esters and amides comprising the surface-active substances including, without limitation, octanoic, decanoic, lauric, tridecanoic (oxo process), myristic, palmitic, arachidic, behenic, carnaubic, stearic, pentadecanoic (0x0 process), oleic, myristoleic and palmitoleic acids, and mixtures of such as acids, such as coconut oil acid, peanut oil acid, safflower -oil acid, linseed oil acid, and tall oil acid.
  • acids RCO H include, without limitation, octanoic, decanoic, lauric, tridecanoic (oxo process), myristic, palmitic, arachidic, behenic, carnaubic, stearic, pentadecanoic (0x0 process), oleic, myristoleic and palmitoleic acids
  • surface-active substances of the type described above are sold commercially under the trade names Igepon A and Igepon T.
  • suitable surface-active substances include, without limitation the lauric acid ester of sodium isethionate, the palmitic acid ester of potassium isethionate, the i-tridecanoic acid ester of sodium isethionate, the myristic acid ester of sodium isethionate, the stearic acid ester of sodium isethionate, the myristoleic acid ester of sodium isethionate, the coconut oil acid and oleic acid esters of sodium isethionate, sodium N-cyclohexyl-N- palmitoyl-taurate, sodium N-methyloleoyltaurate, sodium N-coconut acid -N-methyl-t-aurate, potassium N-i-propyl-N-myristoyl-taurate, sodium N-methyl- N-tallow acid-taurate, sodium N-methyl-M-tall oil acid
  • the water-insoluble powders contemplated for utilization in the present invention are any water-insoluble or very slightly water-soluble solid powders conventionally employed or adapted to be employed in the preparation of wettable powder formulations.
  • Suitable powders include, without limitation, pesticidal powders active as insecticides, nematocides, fungicides, bactericides, tickacides, miticides, herbicides, and the lke, such as sulfur, DDT (1,1,l-trchloro-2,2'-di[p-chlorophenyl]ethane) Lindane gamma-1,2,3,4,5,6-hexachlorocyclohexane) tetramethylthiuram disulfide, zinc ethylene bisdithiocarbamate, Aldrin (1,2,3,4,l0,l0-hexachloro-l,4,4a,S,8,8a-hexahydrol,3,S,8a-endo, exodimethanonaphthalene
  • a portion of the water-insoluble powder ingredient of the wettable powder formulations of the invention may be present as an inert filler or diluent.
  • the primary powder ingredient desired in the formulations such as a powder having pesticidal activity in a formulation to be used as a pesticide, is referred to hereinafter in the specification and claims as the active powder ingredient.
  • the amount of the diluent powder present suitably may range up to about 300 parts by weight and higher, per parts of the active powder ingredient.
  • the particular inert diluent powder employed in a specific embodiment of the formulations of the invention depends, inter alia, upon the nature of the active powder ingredient and the contemplated use of the wettable powder formulation.
  • diluent powders employed include, without limitation, clays, such as Barden clay, attapulgite, bentonite, and kaolinite, diatomaceous earth, fullers earth, calcium limes, calcites, dolomites, gypsum, chalk, mica, talc, silicas, pyrophyllites, reprecipitated calcium o-phosphates and calcium carbonates, as well as other water-insoluble powders of natural or synthetic origin.
  • clays such as Barden clay, attapulgite, bentonite, and kaolinite, diatomaceous earth, fullers earth, calcium limes, calcites, dolomites, gypsum, chalk, mica, talc, silicas, pyrophyllites, reprecipitated calcium o-phosphates and calcium carbonates, as well as other water-insoluble powders of natural or synthetic origin.
  • clays such as Barden clay, attapulgite, bentonite, and kaolinite
  • Water soluble ligninsulfonates employed for the purpose of this invention are, for example, the sodium, cal cium, and magnesium salts of ligninsulfonic acid and also of partly desulfonated ligninsulfonic acid such as those disclosed in US. Patent 2,371,136.
  • Such materials are well known and commercially available and are sold for example under trade names Dazad 23 and Polyfon H (sodium ligninsulfonates), Marasperse C (calcium ligninsulfonate), Marasperse N (sodium ligninsulfonate), Marasperse 'CN (partly desulfonated calcium ligninsulfonate), Darvan 2 (purified sodium ligninsulfonate), and Maratak A and Super Spruce (magnesium ligninsulfonates).
  • alkyl naphthalene sulfonates are well known in the art and are sold under such trade names as Nekal BX (General Aniline & Film Corporation), Maspertine (Du Pont), Marcowet 446C (Chas. Pfizer), Naccosal A (Allied Chemical Co.), Neomerpin N (Du Font), and Alkanol B (Du Pont). These are used in the form of their alkali metal (usually sodium) or ammonium salt. Specific compounds of this type are disclosed in Schwartz & Parry, Surface Active Agents, Interscience Publishing, New York (1949), pp. 116-119 and include monoand dipropyland butyl-naphthalene sulfonates.
  • nonionic surfactant as employed herein in the specification and claims is intended to refer to any conventional nonionic compound having surface-active properties and mixtures of such compounds.
  • suitable nonionic surfactants include, without limitation, the ethylene oxide ethers of alkyl phenols, such as the nonylphenol polyoxyethylene ethers; the ethylene oxide ethers of fatty alcohols, such as tridecyl alcohol polyoxyethylene others; the ethylene oxide ethers of alkyl mercaptans, such as dodecyl mercaptan polyoxyethylene thioethers; and ethylene oxide esters of the fatty acids, such as the lauric acid esters of polyethylene glycols and lauric acid esters of methoxypolyethylene glycols; the ethylene oxide ethers of fatty acid amides, such as the condensation products of lauramide and polyethylene glycols; the condensation products of ethylene oxide with partial fatty acid esters of sorbitol, such as the lauric esters of sorbi
  • the nonionics sold commercially as Igepals and Tritons, i.e., alkyl-aryloxypoly(ethyleneoxy)ethanols, are utilized as the nonionic surfactant ingredient.
  • the acid material employed in the present invention is selected from the group consisting of rosin acids, higher fatty acids having from about 12 to about 20 carbon atoms, mixtures of such acids, mixtures of acids having from about 8 to about 22 carbon atoms, wherein the mixture is characterized by having an average of from about 12 to about 20 carbon atoms per molecule, alkali metal soaps of these acids, and mixtures of such acids and soaps.
  • Example I In evaluating the properties of the wetting agents of the invention in preparing wettable powder formulations, various surface-active compounds and combinations of The fatty acid material may straight P branched in surface-active compounds were tested as the wetting agent structure, and saturated or unsaturated in nature.
  • Speingredient in a pesticidal powder formulation having the c1fic examples of suitable acid materials include, withfollowing basic formulation out limitation, lauric, tridecanoic (oxo process), myristic, I palmitic, stearic, arachidic, oleic, linoleic, myristoleic, ig fg Percent by Wclght palmitoleic, abietic, hydrogenated abietic, and dispropor- P 75 tionated abietic acids, coconut oil acid, tallow oil acid, g d soybean oil acid, peanut oil acid, tall oil fatty acid, tall at en 0 ay 7 oil, and the sodium and potassium soaps of such acids Manisperse N and acid mixtures.
  • the pres- Wettmg agent ent invention tallow oil acid and sodium soap is utilized
  • the wetting agent was first absorbed on a basic inert caras the acid material. rier, Micro-Col, to present an acceptable free-flowing pow- In preparing the wettable powder formulations of the der.
  • the usual ratio was 70 parts wetting agent to 30 parts present invention it will be understood that supplemental Micro-Col.
  • the other ingredients were manually mixed water-soluble or insoluble agents functioning as watertogether with the wetting agent.
  • the formulation was conditioning agents, coloring agents, and the like suitthen micro-pulverized and finally air-milled through a ably may be added. For example, in the pesticidal wettwo-inch air micronizer.
  • the finished formulations were table powders, of the invention, supplemental adjuvants, tested for wetting, foaming, and dispersing properties in including, inter alia, water conditioners, such as sodium accordance with test procedures adapted from the specpolyphosphates, thickening agents, such as casein, gelaific-ations of the World Heath Organization, International tin, carboxymethylcellulose, gums, and oxidized polyethyl- Cooperation Administration, and the United States Govene wax, extender resins, such as coumarone-indene resins, ernment.
  • water conditioners such as sodium accordance with test procedures adapted from the specpolyphosphates
  • thickening agents such as casein, gelaific-ations of the World Heath Organization, International tin, carboxymethylcellulose, gums, and oxidized polyethyl- Cooperation Administration, and the United States Govene wax
  • extender resins such as coumarone-indene resins, ernment.
  • the ingredients employed tion is added to a 250 milliliter beaker containing 100 suitably may be combined inany sequence in any convenmilliliters of standard hard water (342 p.p.m.).
  • the time tional mixing means For example, all of the ingredients required to completely wet the entire sample is noted. initially may be combined in granular form and the mix- An acceptable wetting time is considered'to be less than ture subsequently reduced to powder form in a ball mill three minutes, which is the requirement of the Internaand the like, or the separate ingredients initially may be tional Cooperation Administration specification.
  • Marasperse N (recommended usage) 300 2 0 14 2 7 Atlox WA 1.05% active (2.1% as is) plus 1.5% Marasperse N e. -300 2 1 33 0.2 80 Igepal 00-630, 20 Igepal C 0-210 90 1 0 38 0. 9 so Agent r, 20 Agent g 14 1 0 41 0. 3 80 Agent a, 20 Agent h'" 210 1 0 8 2, 5 80 Agent i, 20 Igepal CO210 90 1 0 2 3. 4 88 Agent k. '12 Agent 1 75 2 0 50 0.1 90 Igepal 00-430, 10 Agent 1 110 3 0 38 0.8 20 Igepon T, 80 Igepal UO430 80 2 1 41 0.
  • This slurry is transferred dicat ion f the s spensi' ili y Power the A dispersing- I to a clean 74 micron sieve and washed with a moderately Wetting agent Without the necessity of 1englhy ahalysisvigorous spray of water at arate of 4 to Sliters per minagents due to the slow wetting and low suspensibility pow- T e f m h test wou1'd 5 P F 15 ute for minutes.
  • the slurry is then washed. with yer f Powders prepared th f on tha other hand hard water into a 250' milliliter graduated cylinder and i ill b apparentthat powders formulated in acmrdance I diluted to'250 milliliters.
  • the cylinder is stopered and rewith the present inventionshow excellent over-all proper- P y inverted through Complete cycles Within one ties. minute.
  • the cylinder is then allowed to stand undisturbed Example II I I at room temperature for 30 minutes. At the end of the 30 minute period the top 225 milliliters of. the'suspension is siphoned oh. with a minimum of disturbance.
  • a pesticidal wettable powder formulation comprising (A) a water-insoluble pesticidal powder, (B) from about 0.3 to about 25 parts by weight per 100 parts said powder of a dispersing agent selected from the group consisting of water-soluble lignin sulfonates and alkyl naphthalene sulfonates, and (C) from about 0.3 to about 25 parts by weight per 100 parts said powder of a wetting agent consisting of a mixture of (1) a surface-active substance of the formula R( iX(CH2)2 O3M (I) wherein R is an acyclic hydrocarbon radical, said surfaceactive substance having an average of from about 10 to about 22 carbon atoms per molecule in R, M is an alkali metal, and X is selected from the group consisting of O and wherein R is selected from the group consisting of hydrogen, alkyl having from 1 to about 6 carbon atoms, and cycloalkyl having from 3 to about 8 carbon atoms; (2) from about to about
  • nonionic surfactant is an alkylaryloxypoly(ethyleneoxy)ethanol.

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  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
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Description

United States Patent 3,342,581 PESTICIDAL WETTABLE POWDER FQRMULATION Fred E. Woodward, Plainfield, N.J., and Andrew Stefcik,
Easton, Pa., assignors to General Aniline & Film Corporation, New York, N.Y., a corporation of Delaware No Drawing. Filed May 20, 1963, Ser. No. 281,801
12 Claims. (Cl. 71-65) This invention relates to wettable powders, and more particularly to wettable powders which are capable of being readily dispersed in Water to form relatively stable, low-foaming aqueous dispersions. The invention also relates to a wetting agent excellently adapted for utilization in the preparation of readily dispersible wettable powder formulations.
The utilization of supplemental agents having wetting, dispersing, and/0r suspending properties is widespread in the preparation of formulations containing water-insoluble powders, such as insecticides, herbicides, fungicides, nematocides, fertilizers, and other industrially employed powders, to render the powders dispersible in water. In the ideal situation the wettable powder formulations are fast wetting when dispersed in water and form suspensions having relatively high solids contents which are low foaming and do not exhibit tendencies toward sedimentation with age. With the increased usage of wettable poW- ders, particularly pesticidal wettable powders, attempts have been made in the art to find supplemental wetting and dispersing agents which are capable of providing wettable powders having the desired characteristics. Such attempts heretofore, however, have not proven to be completely successful and the resulting wettable powder formulations undesirably have been deficient in at least one of the wetting, suspensibility, or foaming categories. Accordingly, due to the absence of more suitable wetting and dispersing agents, industry has been forced to utilize wettable powder formulations which have less than the desired characteristics.
For example, alkyl sulfo esters, i.e., esters of sodium isethionate and long chain fatty acids of the formula RCOOCH CH SO M and alkyl sulfo amides, i.e., substituted amides of sodium aminoethionate and long chain fatty acids of the formula R0 0l ICHzCH2S 03M wherein M is alkali metal, R is an aliphatic hydrocarbon radical of -22 carbon atoms and R is H or lower alkyl (1-6 carbon atoms) or cycloalkyl (3-8 carbon atoms), are commonly employed as wetting-dispersing agents in preparing pesticidal wettable powders. The resulting powders are characterized by excellent Wetting and suspensibility properties, but undesirably form aqueous dispersions which are relatively high foaming. Consequently, suspensions formed from such powders are incapable of being used completely satisfactorily in many types of application equipment. Moreover, due to the formation of foam upon the use of a dispersion containing the powder, an appreciable portion of the powder is trapped therein with a corresponding reduction in the efiiciency of the particular treatment contemplated.
One conventional alternative approach in preparing pesticidal wettable powders involves the utilization of nonionic surface active agents. Although suspensions prepared from the resulting powders exhibit lower foaming than those obtained from Igepons, the nonionic-containing powders heretofore available are slower wetting, generally inferior with respect to suspensibility, and demonstrate a tendency to flocculate.
Accordingly, it is the primary object of the present invention to provide a wettable powder which has superior over-all properties as compared to wettable powders heretofore available.
It is another object of the present invention to provide a wettable powder which is characterized by relatively fast wetting properties.
It is an additional object of the present invention to provide a wettable powder which can be easily dispersed in water to form a relatively stable suspension which advantageously exhibits little tendency toward sedimentation, even with age.
It is still a further object of the present method to provide a wettable powder which is readily dispersible in water to form a relatively low-foaming suspension.
It is a particular object of the present invention'to provide a wettable pesticidal powder which is fast wetting in water and forms aqueous suspensions characterized by excellent suspensibility and low-foaming properties.
It is another particular object of the present invention to provide a wetting agent which is excellently adapted for utilization in the preparation of wettable powder formulations.
Broadly described, the present invention provides a wetting agent for utilization in preparing wettable powders, said wetting agent comprising 1) a surface-active substance of the formula wherein R is an acyclic hydrocarbon radical, said surface-active substance having an average of from about 10 to about 22 carbon atoms per molecule in R, M is an alkali metal, and X is selected from the group consisting of O- and N wherein R is selected from the group consisting of hydrogen, alkyl having from 1 to about 6 carbon atoms, and cycloalkyl having from 3 to about 8 carbon atoms; (2) from about 5 to about 50 parts by weight per parts of said surface-active substance of a nonionic surfactant; and (3) from 0 to about 50 parts by weight per 100 parts said surface-active substance of an acid material having an average of from about 12 to about 20 carbon atoms per molecule selected from the group consisting of rosin acids, fatty acids, alkali metal soaps of said acids, and mixtures thereof.
The present invention also provides a wettable powder formulation comprising (A) a water-insoluble powder,
(B) from about 0.3 to about 25 parts by weight per 100 parts said powder of a dispersing agent selected from the group consisting of water-soluble lignin sulfonates and alkyl naphthalene sulfonates and (C) from about 0.3 to about 25 parts by weight per 100 parts said powder of a wetting agent consisting of a mixture of (1) a surfaceactive substance of the formula surface-active substance of a nonionic surfactant; and (3) from to about 50 parts by weight per 100 parts of said surface-active substance of an acid material having an average of from about 12 to about 20 carbon atoms per molecule selected from the group consisting of rosin acids, fatty acids, alkali metal soaps of said acids, and mixtures thereof.
The surface-active substance employed in the wetting agents and wettable powders of the invention includes a single compound corresponding to Formula 1, given hereinabove, wherein R has from about to about 22 carbon atoms, mixtures of such compounds, and mixtures of compounds corresponding to Formula I wherein R has from about 7 to about 24 carbon atoms and the average number of carbon atoms per molecule in the radical R is in the range of from 10 to about 22. The radical R may be straight or branched-chain in structure and saturated or unsaturated in nature. For example, R may be n-heptyl, n-nonyl, n-decyl, n-undecyl, i-dodecyl, n-tridecyl, i-tetradecyl, n-heptadecyl, n-tridecenyl, n-tetradecenyl, n-heptadecenyl, eicosyl, n-heneicosyl, decosyl, tetr-acosyl, and the like. Such radicals are obtained by the use of acids RCO H, in preparing the esters and amides comprising the surface-active substances including, without limitation, octanoic, decanoic, lauric, tridecanoic (oxo process), myristic, palmitic, arachidic, behenic, carnaubic, stearic, pentadecanoic (0x0 process), oleic, myristoleic and palmitoleic acids, and mixtures of such as acids, such as coconut oil acid, peanut oil acid, safflower -oil acid, linseed oil acid, and tall oil acid.
Surface-active substances of the type described above are sold commercially under the trade names Igepon A and Igepon T. Specific examples of suitable surface-active substances include, without limitation the lauric acid ester of sodium isethionate, the palmitic acid ester of potassium isethionate, the i-tridecanoic acid ester of sodium isethionate, the myristic acid ester of sodium isethionate, the stearic acid ester of sodium isethionate, the myristoleic acid ester of sodium isethionate, the coconut oil acid and oleic acid esters of sodium isethionate, sodium N-cyclohexyl-N- palmitoyl-taurate, sodium N-methyloleoyltaurate, sodium N-coconut acid -N-methyl-t-aurate, potassium N-i-propyl-N-myristoyl-taurate, sodium N-methyl- N-tallow acid-taurate, sodium N-methyl-M-tall oil acidtaurate, and sodium N-n-hexyl -N-palmit-oyl-taurate.
The water-insoluble powders contemplated for utilization in the present invention are any water-insoluble or very slightly water-soluble solid powders conventionally employed or adapted to be employed in the preparation of wettable powder formulations. Suitable powders include, without limitation, pesticidal powders active as insecticides, nematocides, fungicides, bactericides, tickacides, miticides, herbicides, and the lke, such as sulfur, DDT (1,1,l-trchloro-2,2'-di[p-chlorophenyl]ethane) Lindane gamma-1,2,3,4,5,6-hexachlorocyclohexane) tetramethylthiuram disulfide, zinc ethylene bisdithiocarbamate, Aldrin (1,2,3,4,l0,l0-hexachloro-l,4,4a,S,8,8a-hexahydrol,3,S,8a-endo, exodimethanonaphthalene), Isodrin (stereoisomer of Aldrin having the endo, endo configuration), Dieldrin (the 6,7-epoxy derivative of Aldrin), Endrin (the endo, endo isomer of Dieldrin), Captan (N-[trichloromethylthio]-4-cyclohexene 1,2-dicarboximide), 2,4-D (2,4-dichlorophenoxyacetic acid), cuprous oxide, copper oxychloride), copper arsenate, N,N'-dimethylurea, maleic hydrazide, Malathion (S-[1,2-dicarbethoxyethyl] -0,0-dimethyl phosphorodithioate, Parathion (0,0-diethyl-O- nitrophenyl phosphorothioate), Ov-atram (4-ch1orophenyl- 4-chlorobenzene sulfonate), etc., and powdered materials employed in industrial formulations including carbon, silica, calcium carbonate, mica, talc, montmorillonoid clays, such as bentonite, pigments, such as metallic aluminum and copper phthalocyanine, etc.
A portion of the water-insoluble powder ingredient of the wettable powder formulations of the invention may be present as an inert filler or diluent. The primary powder ingredient desired in the formulations, such as a powder having pesticidal activity in a formulation to be used as a pesticide, is referred to hereinafter in the specification and claims as the active powder ingredient. The amount of the diluent powder present suitably may range up to about 300 parts by weight and higher, per parts of the active powder ingredient. The particular inert diluent powder employed in a specific embodiment of the formulations of the invention, depends, inter alia, upon the nature of the active powder ingredient and the contemplated use of the wettable powder formulation. Specific examples of diluent powders employed, include, without limitation, clays, such as Barden clay, attapulgite, bentonite, and kaolinite, diatomaceous earth, fullers earth, calcium limes, calcites, dolomites, gypsum, chalk, mica, talc, silicas, pyrophyllites, reprecipitated calcium o-phosphates and calcium carbonates, as well as other water-insoluble powders of natural or synthetic origin. It will be noted that in one instance a substance may be present as the active powder ingredient of a particular wettable powder formulation and in another instance as an inert diluent powder. The classification of the powder in each particular instance, of course, depends upon the contemplated use of the powder formulation.
Water soluble ligninsulfonates employed for the purpose of this invention are, for example, the sodium, cal cium, and magnesium salts of ligninsulfonic acid and also of partly desulfonated ligninsulfonic acid such as those disclosed in US. Patent 2,371,136. Such materials are well known and commercially available and are sold for example under trade names Dazad 23 and Polyfon H (sodium ligninsulfonates), Marasperse C (calcium ligninsulfonate), Marasperse N (sodium ligninsulfonate), Marasperse 'CN (partly desulfonated calcium ligninsulfonate), Darvan 2 (purified sodium ligninsulfonate), and Maratak A and Super Spruce (magnesium ligninsulfonates).
Likewise the alkyl naphthalene sulfonates are well known in the art and are sold under such trade names as Nekal BX (General Aniline & Film Corporation), Maspertine (Du Pont), Marcowet 446C (Chas. Pfizer), Naccosal A (Allied Chemical Co.), Neomerpin N (Du Font), and Alkanol B (Du Pont). These are used in the form of their alkali metal (usually sodium) or ammonium salt. Specific compounds of this type are disclosed in Schwartz & Parry, Surface Active Agents, Interscience Publishing, New York (1949), pp. 116-119 and include monoand dipropyland butyl-naphthalene sulfonates.
The term nonionic surfactant as employed herein in the specification and claims is intended to refer to any conventional nonionic compound having surface-active properties and mixtures of such compounds. Examples of suitable nonionic surfactants include, without limitation, the ethylene oxide ethers of alkyl phenols, such as the nonylphenol polyoxyethylene ethers; the ethylene oxide ethers of fatty alcohols, such as tridecyl alcohol polyoxyethylene others; the ethylene oxide ethers of alkyl mercaptans, such as dodecyl mercaptan polyoxyethylene thioethers; and ethylene oxide esters of the fatty acids, such as the lauric acid esters of polyethylene glycols and lauric acid esters of methoxypolyethylene glycols; the ethylene oxide ethers of fatty acid amides, such as the condensation products of lauramide and polyethylene glycols; the condensation products of ethylene oxide with partial fatty acid esters of sorbitol, such as the lauric esters of sorbitan polyethylene glycol ether; and other similar materials. In the preferred embodiments of the wetting agents and wettable powder formulations of the present invention, the nonionics, sold commercially as Igepals and Tritons, i.e., alkyl-aryloxypoly(ethyleneoxy)ethanols, are utilized as the nonionic surfactant ingredient.
The acid material employed in the present invention is selected from the group consisting of rosin acids, higher fatty acids having from about 12 to about 20 carbon atoms, mixtures of such acids, mixtures of acids having from about 8 to about 22 carbon atoms, wherein the mixture is characterized by having an average of from about 12 to about 20 carbon atoms per molecule, alkali metal soaps of these acids, and mixtures of such acids and soaps.
Example I In evaluating the properties of the wetting agents of the invention in preparing wettable powder formulations, various surface-active compounds and combinations of The fatty acid material may straight P branched in surface-active compounds were tested as the wetting agent structure, and saturated or unsaturated in nature. Speingredient in a pesticidal powder formulation having the c1fic examples of suitable acid materials include, withfollowing basic formulation out limitation, lauric, tridecanoic (oxo process), myristic, I palmitic, stearic, arachidic, oleic, linoleic, myristoleic, ig fg Percent by Wclght palmitoleic, abietic, hydrogenated abietic, and dispropor- P 75 tionated abietic acids, coconut oil acid, tallow oil acid, g d soybean oil acid, peanut oil acid, tall oil fatty acid, tall at en 0 ay 7 oil, and the sodium and potassium soaps of such acids Manisperse N and acid mixtures. In preferred embodiments of the pres- Wettmg agent ent invention tallow oil acid and sodium soap is utilized The wetting agent was first absorbed on a basic inert caras the acid material. rier, Micro-Col, to present an acceptable free-flowing pow- In preparing the wettable powder formulations of the der. The usual ratio was 70 parts wetting agent to 30 parts present invention it will be understood that supplemental Micro-Col. The other ingredients were manually mixed water-soluble or insoluble agents functioning as watertogether with the wetting agent. The formulation was conditioning agents, coloring agents, and the like suitthen micro-pulverized and finally air-milled through a ably may be added. For example, in the pesticidal wettwo-inch air micronizer. The finished formulations were table powders, of the invention, supplemental adjuvants, tested for wetting, foaming, and dispersing properties in including, inter alia, water conditioners, such as sodium accordance with test procedures adapted from the specpolyphosphates, thickening agents, such as casein, gelaific-ations of the World Heath Organization, International tin, carboxymethylcellulose, gums, and oxidized polyethyl- Cooperation Administration, and the United States Govene wax, extender resins, such as coumarone-indene resins, ernment. The following is a brief description of each test also may be incorporated into the formulation. employed: In preparing the wetting agents and wettable powder Wetting-A five gram sample of the finished formulaformulations of the invention, the ingredients employed tion is added to a 250 milliliter beaker containing 100 suitably may be combined inany sequence in any convenmilliliters of standard hard water (342 p.p.m.). The time tional mixing means. For example, all of the ingredients required to completely wet the entire sample is noted. initially may be combined in granular form and the mix- An acceptable wetting time is considered'to be less than ture subsequently reduced to powder form in a ball mill three minutes, which is the requirement of the Internaand the like, or the separate ingredients initially may be tional Cooperation Administration specification. The rereduced to powder form by any conventional technique vised World Heath Organization specification carries no and thenall mixed-together. wetting requirement, although the earlier specification re- The invention having been broadly described, the folquired an acceptable formulation to have a wetting time lowing examples are given to show specific embodiments of less than one minute. thereof. It will be understood that the examples are given Foam and sediment.The material used in the wetting for illustration purposes and not by way of limitation. test is stirred and drained into a milliliter graduate,
TABLE 1 Foam Ht. 1n mls. Sedi- Run Wetting Agent Wetting ment Solids No. (See) (m1) (percent) Immed. 30Mins.
Igepon T 3o 10 5 2 3.1 Igepon CN-42 120 1 0 23 1. 6 Igepal 00-430 1 0 4 3. 3 Igcpal 00-630 9o 1 0 1 2. 5 Igepal DM-430 240 2 0 4 3. 1 Agent a 165 l 0 7 2. 6 Agent b 300 3 0 25 0. 4 Agent 0 200 2 0 42 0. 2 Agent (1 1 o 32 1. 2 Agent e 2 2 2 3. 4 Atlox WA II 1.05% active (2.1% as is) plus 1.5%
Marasperse N (recommended usage) 300 2 0 14 2 7 Atlox WA 1.05% active (2.1% as is) plus 1.5% Marasperse N e. -300 2 1 33 0.2 80 Igepal 00-630, 20 Igepal C 0-210 90 1 0 38 0. 9 so Agent r, 20 Agent g 14 1 0 41 0. 3 80 Agent a, 20 Agent h'" 210 1 0 8 2, 5 80 Agent i, 20 Igepal CO210 90 1 0 2 3. 4 88 Agent k. '12 Agent 1 75 2 0 50 0.1 90 Igepal 00-430, 10 Agent 1 110 3 0 38 0.8 20 Igepon T, 80 Igepal UO430 80 2 1 41 0. 7 50 Igepon T, 50 Igepal 00-430. 60 7 5 22 1. 7 80 Igepon T, 20 Igepal 00-430 26 5 4 0 4 2 r 1 Sodiurn-N-methyl-N-oleoyl-taurate. Y Y
2 Sodium-N -cyclohexyl-N-pal.1nitoyltaurate. 3 N onylphenoxypoly(ethyleneoxy)ethanol, sp. gr. 1.02-1.03. 4 N onylphenoxypoly(ethyleneoxy)ethanol, sp. gr. 1.05-1.07:
5 Dinonylphenoxy poly(ethyleneoxy)ethanol, Sp. gr. 0990 1.000.
fl Dinonylphenoxy poly(ethyleneoxy)ethanol, sp. gr. 1.02. 7 N onylpheuoxy poly(ethyleneoxy)ethyl chloride. 8 Sodium salt of complex organic phosphate ester. Sodium salt of complex organic phosphate ester. Sodium N -methyl-N -stearoyl-taurate. l1 Atlas Chemical Industries, wetting agent for Wettable Pesticidal Powders. l2 Nonylphenoxypoly(ethyleneoxy)ethano1, sp. gr. 0.98-0.99. 13 Dinonylphenoxy poly(ethyleneoxy)ethanol. sp. gr. 1.04-1.05. 14 Dinonylphenoxy poly(ethyleneoxy) ethanol. 15 Condensation product of dinonylphenol plus 1.5 moles of ethylene oxide Alkylpoly(ethyleneoxy)ethanol, sp. gr. 0.98.
11 Nonylphenoxypoly(ethyleneoxy) ethanol. 15 N onylphenoxypoly(ethyleneoxy)ethanol, sp. gr. 1.18. 19 Sulionated aliphatic polyester.
7 8 stoppered, and repeatedly inverted through twenty com- Tropical heat storage.-Twenty grams of the wettable plete cycles. Foam in milliliters is noted immediately after powder tested, formulated as in Example I, are placed the agitation is stopped and again after allowing the samin a 250 milliliter beaker. A loose fitting disc is placed plc to stand undisturbed for thirty minutes. The sediment on the powder and weighted to exert an even pressure of level is also noted and recorded at the same points in 5 25 grams per square centimeter thereon. The beaker is time. No absolute limits'are employed as standards, 211- then placed in an, oven at 55 C- for 24 hours, after though relatively, low levels of both foam and sediment which the pressure assembly'is removed and the powder is are desirable. allowed to cool at room temperature. The following tests Suspensibility.-'Ihe top 50 milliliters of solution used are then run on the powder three hours after removal in the foam and sediment testis withdrawn from the grad- 10 from the oven. uate and evaporated to dryness to determine the percent- Sieving.-Ten grams of the pretreated powder is slurried age of Solids thel'eih- The figure Obtained gives an with 100 milliliters of tap water. This slurry is transferred dicat ion f the s spensi' ili y Power the A dispersing- I to a clean 74 micron sieve and washed with a moderately Wetting agent Without the necessity of 1englhy ahalysisvigorous spray of water at arate of 4 to Sliters per minagents due to the slow wetting and low suspensibility pow- T e f m h test wou1'd 5 P F 15 ute for minutes. The residue remaining on the sieve is lfldwatmg a perfect dlsperslom i test a f evaporated to dryness and weighed, The World Health of 3 World B i orgamzanon Imematmnali Organization specifications require that not more than 2% cooperafflon dq i (dry weight) of the powder sample treated shall re- The results of these initial testsappear in Table 1., main on the siev when tested in this manner It can be seen from the results tabulated above that 0, suspensibilitylwA Sample of 8 33 gfams the p th A ld I i g g i g ggg 3355 35 22 g: g i gzi giig Es s treated powder is slu'rned with 30 milliliters of standard hard water in a 100 milliliter beaker and allowed to in themselves are'not com letel satisfactor as wettiu y P y y stand for 15 minutes. The slurry is then washed. with yer f Powders prepared th f on tha other hand hard water into a 250' milliliter graduated cylinder and i ill b apparentthat powders formulated in acmrdance I diluted to'250 milliliters. The cylinder is stopered and rewith the present inventionshow excellent over-all proper- P y inverted through Complete cycles Within one ties. minute. The cylinder is then allowed to stand undisturbed Example II I I at room temperature for 30 minutes. At the end of the 30 minute period the top 225 milliliters of. the'suspension is siphoned oh. with a minimum of disturbance. The remain- I ing 25 milliliters'of suspension are analyzedfor DDT and Formulations prepared'in accordance with the inven 30 'tion and others preparedutilizing diiierent formulas for the wetting agents were tested initially with the procedure d ib d in Example I and than portions of the, f l the sus'pensib'ility is calculated in accordance with the tions were tested in a second series of tests for wetting, World Health Organization Specification, which requires sieving, and suspensibility carried out after a tropical heat that a m of 50% 0f the i l mple Shall be in storage according to thelnternational Cooperation Assosuspension when tested in this manner.- p ciation and the World Health Organization specifications. The results of the tests are set forth below in Tables The manner of carrying out these tests appears below: 2 and 3:
TABLE 2.PERFORMANCE OF FORMULATIONS BEFORE TROPICAL HEAT STORAGE Foam. Ht. in 11115. Sedi- Run Wetting Agent Wetting merit Solids N 0. (Sec.) (1111.) (percent) Immed. 30Mins.
22 Igepon T-77..- 30 10 5 2 3 1 Igepal (JO-430- 180 3 0 3 3. 2 Atlox WA at 1%. 300 2 O 14 2. 7 Atlox WA at 2.1% 300 2 1 33 0. 2 Agriwet 9086 1 at 1.5%-... 130 6 5 3 24 0. 9 Agriwet 9086 at 2.5% 70 6 5 1 5. 4 28 80 Agent i, 20 Igepal C0-2l0. 180 4 0 20 1. 2 29 72 Igepon T-43, l8 Igepal CO 430 10 Igepal 00-210 56 8 5 2 3. 2 30 80 Igepon T-43, 20 Igepal 00-430 38 5 3 1 3. 5 72I1lgeip0n T 13, 18 Igepal 00-430, 10 Amber 32 6 1 1 3.5
1 a 'OS. 72 Igepon T-43, 18 Igepal 00-430, 10 Tallow 49 4 3 1 3. 5
Fatty Acid.
1 Nopco Chemical 00., wetting agent for Pesticidal Wettable Powders. 2 Tallow Fatty Acid, Sodium Salt. 3 Flocculated. TABLE 3.-PERFORMANCE OF FORMULATIONS AFTER TROPICAL HEAT STORAGE Run Wetting Sieve Sediment Suspensi- No. Wetting Agent (Sec.) Residue (1311.) y
(percent) (percent) Specification Requirement--- 180 2 50 33- Igepon T-77 8 1.1 8 74 34- Igepal CO430- 180 0. 6 17 73 35----- Atlox WA at 1% 38 6. 3 1 73 Atlox WA at 2.17 38 4. 9 1 Agriwet 9086 at 1.5%. 30 11. 4 1 32 48 Agriwet 9086 at 2.5% 20 0.03 12 72 Agent i, 20 Igepal (DO-210 180 1. 8 1 33 55 72 Igepon T-43, l8 Igepal 00-430, 10 Igepal 00-210. 12 0. 1 21 41 80 Igepou T-43, 20 Igepal 00-430 8 0. 1 15 66 72 Igepon T-43, l8 Igepal CO430, 10 Amber Flakes. 7 0. 1 13 74 72 Igeion T-43, l8 Igepal (30-430, 10 Tallow Fatty 7 01 9 1 Flocculated.
The results tabulated in Tables 2 and 3 clearly show the significant improvement obtained with respect to overall properties by the use of the formulations of the invention.
While all of the above tests were carried out using DDT as the active ingredient, it will be appreciated that any of the other conventional toXicants or industrial powders could be used in its place. Moreover, the particular dispersing agent and inert carriers used in the above tests are not to be considered as limitative, since any of the materials well known for these purposes could be substituted for those used in the tests, while maintaining the improved characteristics realized with the wetting agents of the instant invention.
It is to be understood that the foregoing detailed description is given merely by way of illustration and that many variations may be made therein Without departing from the spirit of this invention.
What is claimed is:
1. A pesticidal wettable powder formulation comprising (A) a water-insoluble pesticidal powder, (B) from about 0.3 to about 25 parts by weight per 100 parts said powder of a dispersing agent selected from the group consisting of water-soluble lignin sulfonates and alkyl naphthalene sulfonates, and (C) from about 0.3 to about 25 parts by weight per 100 parts said powder of a wetting agent consisting of a mixture of (1) a surface-active substance of the formula R( iX(CH2)2 O3M (I) wherein R is an acyclic hydrocarbon radical, said surfaceactive substance having an average of from about 10 to about 22 carbon atoms per molecule in R, M is an alkali metal, and X is selected from the group consisting of O and wherein R is selected from the group consisting of hydrogen, alkyl having from 1 to about 6 carbon atoms, and cycloalkyl having from 3 to about 8 carbon atoms; (2) from about to about 50 parts per 100 parts of said surface-active substance of a nonionic surfactant; and (3) from 0 to about 50 parts by weight per 100 parts of said surface-active substance of an acid material having an average of from about 12 to about 20 carbon atoms per molecule selected from the group consisting of rosin acids, higher fatty acids, alkali metal soaps of said acids, and mixtures thereof.
2. The wettable powder according to claim 1 wherein said nonionic surfactant is an alkylaryloxypoly(ethyleneoxy)ethanol.
3. The wettable powder according to claim 1 wherein said fatty acid material is tallow oil acid.
4. The wettable powder according to claim 1 wherein said surface-active substance is the coconut oil acid ester of sodium isethionate.
'5. The wettable powder according to claim 1 wherein said surface-active substance is the oleic acid ester of sodium isethionate.
6. The wettable powder according to claim 1 wherein said surface-active substance is sodium N-cyclohexyl-N- palmitoyl-taurate.
7. The wettable powder according to claim 1 wherein said surface-active substance is sodium N-methyl-N-oleoyltaurate.
8. The wettable powder according to claim 1 wherein said surface-active substance is sodium N-coconut acid- N-methyl-taurate.
9. The wettable powder according to claim 1 wherein said surface-active substance is sodium N-methyl-N-tallow acid-taurate.
10. The wettable powder according to claim 1 wherein said surface-active substance is sodium N-methyl-N-palmitoyl-taurate.
11. The wettable powder according to claim 1 wherein said surface-active substance is sodium N-methyl-N-tal1 oil acid-taurate.
12. The wettable powder according to claim 1 wherein said pesticidal water-insoluble powder consists of up to about 300 parts by weight per parts of said pesticidal water-insoluble powder of an inert diluent.
References Cited UNITED STATES PATENTS 2,642,400 '6/ 1953 Harris 252-353 2,794,004 5/1957 Ratti 252-353 2,858,250 10/1958 Geary 167-42 2,913,372 11/1959 Velde et a1. 16742 2,948,655 8/1960 Flenner 16742 3,068,144 12/1962 Gilbert 167-42 X 3,100,174 8/1963 Stevens 167-42 3,235,357 2/1966 Loux 712.5
FOREIGN PATENTS 670,225 10/ 1953 Canada.
LEWIS GOTTS, Primary Examiner. JULIAN LEVITT, JAMES O. THOMAS, 112., Examiners. D. MOYER, Assistant Examiner.

Claims (1)

1. A PESTICIDAL WETTABLE POWDER FORMULATION COMPRISING (A) A WATER-INSOLUBLE PESTICIDAL POWDER, (B) FROM ABOUT 0.3 TO ABOUT 25 PARTS BY WEIGHT PER 100 PARTS SAID POWDER OF A DISPERSING AGENT SELECTED FROM THE GROUP CONSISTING OF WATER-SOLUBLE LIGNIN SULFONATES AND ALKYL NAPHTHALENE SULFONATES, AND (C) FROM ABOUT 0.3 TO ABOUT 25 PARTS BY WEIGHT PER 100 PARTS SAID POWDER OF A WETTING AGENT CONSISTING OF A MIXTURE OF (1) A SURFACE-ACTIVE SUBSTANCE OF THE FORMULA
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Cited By (9)

* Cited by examiner, † Cited by third party
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US3673087A (en) * 1967-01-05 1972-06-27 Ici Ltd Plant treatment composition comprising a plant treatment chemical, a wetting agent and an aliphatic alcohol
US3877928A (en) * 1967-08-08 1975-04-15 Walter A Houston Liquid soluble packet
US3952105A (en) * 1972-03-27 1976-04-20 Scm Corporation Organometallic agricultural fungicidal compositions and methods for making and using same
US3986979A (en) * 1969-05-15 1976-10-19 Westvaco Corporation Process for making combination wetting-dispersing agent
US4348385A (en) * 1980-11-17 1982-09-07 Mobay Chemical Corporation Flowable pesticides
US4381194A (en) * 1981-02-09 1983-04-26 Westvaco Corporation Alkali lignin based pesticide phytotoxicity reducing composition
DE3333872A1 (en) * 1983-09-20 1985-03-28 Norddeutsche Affinerie AG, 2000 Hamburg GRANULATED COMPOSITION OF AQUEOUS OR INSOLUBLE IN WATER DISPERSABLE IN AQUEOUS MEDIA
US5167694A (en) * 1989-01-19 1992-12-01 Westvaco Corporation Fatty acid and amide wetting agents for pesticide formulations
US5461077A (en) * 1993-10-21 1995-10-24 Great Lakes Chemical Corp. Use of perbromides to control diseases in plants

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US2913372A (en) * 1954-07-23 1959-11-17 Atlas Powder Co Compositions for dispersing powders in water
US2948655A (en) * 1958-04-03 1960-08-09 Du Pont Non-dusty water-dispersible fungicidal composition
US3068144A (en) * 1959-10-22 1962-12-11 Allied Chem Processes of controlling fungi on plants with trichloroisocyanuric acid
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US2642400A (en) * 1950-05-10 1953-06-16 Monsanto Chemicals Surface-active composition
US2913372A (en) * 1954-07-23 1959-11-17 Atlas Powder Co Compositions for dispersing powders in water
US2858250A (en) * 1955-06-13 1958-10-28 Robert J Geary Pesticidal composition containing a water dispersible lignin sulfonic acid
US2948655A (en) * 1958-04-03 1960-08-09 Du Pont Non-dusty water-dispersible fungicidal composition
US3235357A (en) * 1959-08-14 1966-02-15 Du Pont Method for the control of undesirable vegetation
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Cited By (10)

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US3673087A (en) * 1967-01-05 1972-06-27 Ici Ltd Plant treatment composition comprising a plant treatment chemical, a wetting agent and an aliphatic alcohol
US3877928A (en) * 1967-08-08 1975-04-15 Walter A Houston Liquid soluble packet
US3986979A (en) * 1969-05-15 1976-10-19 Westvaco Corporation Process for making combination wetting-dispersing agent
US3952105A (en) * 1972-03-27 1976-04-20 Scm Corporation Organometallic agricultural fungicidal compositions and methods for making and using same
US4348385A (en) * 1980-11-17 1982-09-07 Mobay Chemical Corporation Flowable pesticides
US4381194A (en) * 1981-02-09 1983-04-26 Westvaco Corporation Alkali lignin based pesticide phytotoxicity reducing composition
DE3333872A1 (en) * 1983-09-20 1985-03-28 Norddeutsche Affinerie AG, 2000 Hamburg GRANULATED COMPOSITION OF AQUEOUS OR INSOLUBLE IN WATER DISPERSABLE IN AQUEOUS MEDIA
EP0135963A3 (en) * 1983-09-20 1985-06-19 Norddeutsche Affinerie Ag
US5167694A (en) * 1989-01-19 1992-12-01 Westvaco Corporation Fatty acid and amide wetting agents for pesticide formulations
US5461077A (en) * 1993-10-21 1995-10-24 Great Lakes Chemical Corp. Use of perbromides to control diseases in plants

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