US3102070A - Miticidal compositions - Google Patents

Miticidal compositions Download PDF

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Publication number
US3102070A
US3102070A US109505A US10950561A US3102070A US 3102070 A US3102070 A US 3102070A US 109505 A US109505 A US 109505A US 10950561 A US10950561 A US 10950561A US 3102070 A US3102070 A US 3102070A
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US
United States
Prior art keywords
bis
alkyl
weight
oleate
ethylene oxide
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.)
Expired - Lifetime
Application number
US109505A
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English (en)
Inventor
Gerard C Riley
Edward A Nolan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rohm and Haas Co
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Rohm and Haas Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Priority to US109505A priority Critical patent/US3102070A/en
Priority to BR138794/62A priority patent/BR6238794D0/pt
Priority to GB17529/62A priority patent/GB995383A/en
Priority to ES277137A priority patent/ES277137A1/es
Priority to CH572862A priority patent/CH409513A/fr
Priority to AT390062A priority patent/AT246491B/de
Application granted granted Critical
Publication of US3102070A publication Critical patent/US3102070A/en
Priority to MY196984A priority patent/MY6900084A/xx
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • 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

  • Pesticides such as insecticides and miticides
  • emulsion concentrates and wettable powders for spray purposes, as dusts, and as aerosols.
  • mites In the control of mites on agricultural and horticultural crops, it is common to apply emulsion concentrates or wettable powders in aqueous sprays.
  • a particularly effective miticide for use in such sprays is l,l-bis (p -chlorophenyl) -2,2,2-trichloroetlranol. It is usual practice to use this agent in conjunction with other types of pesticidal agents.
  • emulsion concentrates or wettable powders of these other agents are used in the same aqueous mixture as this miticide.
  • the l,l-bis(halophenyl)-2,2,2-trichloroethanols are miticidal agents, the preparation of which is described in US. Patents No. 2,812,280 and 2,812,362.
  • the product, 1,1-bis(chlorophenyl)-2,2,2 trichloroethanol is a wellknown commercial miticide and there are various pesticidal compositions which utilize it as an active miticide.
  • emulsion concentrates and wettable powder formulations containing a l,l-bis(halophenyl)-2,2,2-trichloroethanol as an active mirticidal agent have been evolved which show excellent compatibility when admixed in a spray tank with other formulated pesticides, which promise favorable miticidal effectiveness under adverse .climatic conditions, and which have acceptable phytotoxic properties.
  • the emulsion concentrates of this invention comprise 1,l-bis(halophenyl)-2,2,2-tnichloroethanol dissolved in an alkyl oleate with the incorporation of emulsifying agent.
  • Emusifying agents are used in the concentration range of about 9 to about 20% by weight based on the emulsifialble concentrate and preferably 10% to 15%.
  • dinitroallcylphenyl especially the dinitro(2- methylheptyl)-phenyl, esters of crotonic, acrylic, methacrylic, 5,,8-dimethylacrylic, and 4 pentenoic acids which have been shown to have miticidal, insecticidal, and fungicidal properties may be advantageously added to these concentrates, and likewise such insecticidal agents as 1,1,1- trichloro-2,2bis (p-chlorophen-yl) ethane, 1, 1-dichloro-2,2- bis(p-chlorophenyl)ethane, or 1,1-dichloro-2,2-bis(ethy1- phenyl)-ethane, phosphatic pesticides such as 0,0-dimethyl S-(LZ-diCBIbdthOXYCt-hfl) dithicphosphate, and l-na-phthyl N-
  • 1,1-bis(halophenyl)-2,2,2-trichloroethanol with pesticidal agents which kill mite predators and which, when used alone, thus cause a build-up of the mite population.
  • pesticidal agents which kill mite predators and which, when used alone, thus cause a build-up of the mite population.
  • pesticidal agents of the above type may be added to an emulsion concentrate. The percentage depends in part on the solubility of the particular pesticidal agent being incorporated.
  • the wettable powder formulations of this invention are made by mixing an inert, finely-divided, solid carrier with the emulsion concentrate.
  • the emulsion concentrate There may be used from 5% to 25% by weight of 1,l bishalophenyl)-2,2,2-trichl0roethanol in such compositions, this compound being dissolved in alkyl oleate together with emulsifiers.
  • the amount of the emulsion concentrate added to the inert solid will vary with the capacity of each individual carrier or combination of carriers to hold the liquid and still maintain the product as a powder of loose texture.
  • the preferred 1,l bis(halophenyl)-2,2,2-trichloroethan- 01 used in this invention is 1,1-bis(p-chlorophenyl)-2,2,2- 'trichloroethanol. It may be used in a pure form or as a technical grade containing isomers having bis(orthochlorophenyl) groups and the p, o dichlorc-dip henyl groups as minor components. Also, the corresponding bromophenyl and fluorophenyl analogs may be used alone or admixed with 1,l-bis(chloropheny1) -2,2,2-trich1oroethanol.
  • the solvent for the preparation of the emulsion concentrates there is used methyl oleate, ethyl oleate, or mixtures of these two.
  • One purpose of the solvent is to act as a plasticizer for the l,l-bis(-halophenyl)-2,2,2-trichloroethanol and thus keep the active ingredient in a fluid condition at low temperatures. It is also desirable to have the emulsion concentrates flowable after prolonged storage at ambient temperatures in cold weather. 'For these reasons the oleic acid ester or mixture of esters used must have a low setting point; i.e., the temperature range wherein a solid forms. This point will vary with purity of the oleates and should be no more than 60 (about 16 C.). There may be used relatively pure alkyl oleates or commercially available technical products.
  • emulsifying agents there may be used surface active ethylene oxide adducts of alkyl mercaptans, long-chained carboxylic acids, higher alcohols, and alkylphenols wherein the ethylene oxide content of the resulting product is about 15 to 100 ether units, preferably 20 to units.
  • the alkyl mercaptans and higher alcohols should have 10 to 20 carbon atoms in their alkyl groups, while the acids should contain 12 to 24 carbon atoms in their carboxylic portion, which may be a straight or branched chain or a cycle, as in abietic acid.
  • Typical of these are t-tetradecylthiopolyethoxyethanol, tall-oil-acid polyethoxyethanol, dodecyloxypolyethoxyethanol, and alkylphenoxypolyethoxyethanol, wherein the alkyl group or groups contain 8 to 12 carbon atoms and the main group occurs preferably in the para position but that position is immaterial.
  • alkyl group or groups contain 8 to 12 carbon atoms and the main group occurs preferably in the para position but that position is immaterial.
  • ethylene oxide adducts -dodecylbenzenesulfonate There may also be used.
  • esters are formed with such long-chained acids as oleic or lauric acids.
  • alkylarenesulfonic aoids wherein the alkyl group or groups contain from 8 to 18 carbon atoms in admixtures with the above described ethylene 'oxide adducts.
  • the preferred sulfonates are salts of alkylbenzenesulfonic acid, such as calcium p-t-dodecylbenzenesulfonate.
  • alkylbenzenesulfonic acid such as calcium p-t-dodecylbenzenesulfonate.
  • similar'alkyl 'naphthalenesulfonic acid salts such as oalcium'octylnaphthalenesulfonates.
  • the ratio of weights of the ethylene oxide adduct to the sulfonate may vary from about 3 :1 to about 1:1.
  • finely dispersed solid carriers for the preparation of these wettable powders are the finely particled clays such as fullers earth and kaolins,
  • silica diatomaceous earth, and alkaline earth silicates
  • dispersing agents I into the wettable powders.
  • these are the salts of polymers formed from maleic anhydride and olefinically unsaturated hydrocarbons such as styrene, alkylstyrenes, or diisobutylene.
  • styrene styrene
  • alkylstyrenes alkylstyrenes
  • diisobutylene diisobutylene.
  • ammonia or some amines are used to form salts, some amide orimide formation also occurs.
  • the amount of the added dispersit has good suspendibility in waters of varying hardness, and its application properties to foliage are entirely acceptable from its aqueous sprays.
  • dispersing agent is a salt of a condensed formaldehyde-naphthalene sulfonate such as sodium formaldehyde-naphthalene sulfonate as sold under the trade names of Daxad or Tamol.
  • ingagent is desirably 1% to 10% of the weight of the powderto which it is added.
  • the resulting emulsion concentrate may be diluted with water to provide an efficient spray for protection against mites. It is compatible Wtih wettable powders containing fungicides such as wettable sulfur, ferbam, zineb, and
  • Example 3 There are mixed 20 pants of technical 1,1-bis(cl1'lorophenyl)-2,2,2-trichloroethanol, 65' parts of methyl oleate (set point about 0 C.), and 15 parts of anemulsifier from 10 parts of long-chained fatty acid-ethylene oxide adduct, having'about ether groups perjmolecule and 5 parts of calcium tetradecylbenzenesulfonate.
  • the resulting emulsion concentrate is stable on storage and is readily dispersed in even hard water to give effective aqueous sprays.
  • the emulsion concentrates of this invention can be readily formulated so as to he acceptably low in phytotoxicity on plants, even on flush citrus growth. Thisis also true of properly formulated wettable powders. 1 Since the alkyl oleates :are very high boiling and havehigh flash points, they can be used in grinding-machinery without hazard. Because of thelow volatility of the alkyl oleates the active agents remain in a fluid and active state. Most important of all, however, is the unusual degree .ofcom- I patibility of compositions of this invention with man common formulations of other pesticides.
  • a miticid-al composition comprising asian active miticidal agent a 1,1-bis(halophenyl)-2,2,2 trichloroethanol dissolved in an alkyl oleate'in which the alkyl group contains one to two carbon atoms together with emulsify- 'ing agents consisting of a surface active ethyleneoxide adduct having 15 to 100 ether units and a-surfaceactive oil-soluble alkylarenesulfon-ate, the ratio of the ethylene oxide adduct to the alkylarenesulfonate varying' from about 3:1 to about 1:1 by weight.
  • a miticidal composition comprising'asian active miticidal agent 1,1-bis(chlorophenyl)-2,2,2-triohloroethanol and emulsifying agents dissolved in an alkyl oleate in which the alkyl group contains one to two carbon atoms, the ratio of said 1,1- bis(chlorophenyl)-2,2,2-trichloroethanol to said alkyl oleate 'being from 1:4 to 1.25 :1 and the emulsifying agents consisting of a surface active ethylene oxide adduct having 15 to 100 ether units and a surface active oil-soluble alkylarenesulfonate, theratio of the ethylene oxide adduct to the ialkylarenesulfonate I varying from about 3:1 to about 1:1 by weight.
  • a miticidal composition in the form of a wettable powder comprising a finely divided inert solidcarrying a solution of 1,1-bis(-chlorophenyl)-2,2,2-trichloroethanol and emulsifying agents in an alkyl oleate in which the arenas/o alkyl group contains one to two carbon atoms, the ratio of said 1,1-bis (chlorophenyl)-2,2,2-trichloroethanol to said alkyl oleate being from 1 :4 to 1.25:1 and the emulsifying agents consisting of a surface active ethylene oxide adduct having to 100 ether units and a surface active oil-soluble alkylarenesu-lfonate, the ratio of the ethylene oxide adduct to the alkylarenesulfonate varying from about 3:1 to about 1:1 by Weight.
  • a rniticidal composition comprising a solution of 1,1-bis(chlorophenyl)-2,2,2-trichloroethancl and emulsifying agents in at least one alkyl oleate in which the alkyl group contains one to two carbon atoms, the ratio of said l,l-bis(chlorophenyl)-2,2,2-trichloroethanol to said alkyl oleate being from 1:4 to 1.25:1 and the emulsifying agents consisting of a surface active ethylene oxide adduct having 15 to 100 ether units and a surf-ace active, oil-soluble alkylbenzenesulfonate wherein the alkyl group contains from 8 to 18 carbon atoms, the ratio of the ethylene oxide adduct to the alkylbenzenesulfonate varying from about 3:1 to about 1:1 by weight, the said emulsifying agents providing about 9% to of the weight of the solution.
  • a miticid al composition in the form of a wettable powder comprising a finely divided inert solid carrying a solution of 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol and emulsifying agents in an alkyl oleate in which the a-llryl group contains one to two carbon atoms, the ratio of said 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol to calcium alkylbenzenesu-lfonate is calcium dodecylbenzenesaid alkyl oleate being from 1:4 to 1.25 :1 land the emulsifying agents consisting of a surface active ethylene oxide adduct having 15 to 100 ether units and a surface active, oil-soluble ialkylbenzenesulfonate wherein the alkyl substituent contains from 8 to 18 carbon atoms, the ratio of the ethylene oxide adduct to the alkylbenzene sulfonate varying from
  • composition according to claim 5 in which there is added to the Wettable powder 1% to 10% by weight of a dispersing agent.
  • composition according to claim 6 in which the dispersing agent is a salt of a polymer of maleic anhydride and diisobutylene.
  • a miticidal composition in the form of a Wettable powder comprising a finely divided hydrated silica carrying a solution of 1,1- bis(chlorophenyl)-2,2,2-trichloroethanol and emulsifying agents in methyl oleate, the ratio of said 1,1-bis-(ch1orophenyl)-2,2,2-trichloroethanol to said methyl oleate being from 1:4 to 1.25:1 and the emulsifying agents consisting of an alkylphenoxypolyethoxyethanol having 20 to 70 ether units and containing 8 to 12 carbon atoms in its alkyl substituent and a surface active, oil-soluble calcium alkylbenzenesulfonate wherein the alkyl substituent contains from 8 to 18 carbon atoms, the ratio of the alkylphenox'ypolyethoxyethanol to the calcium alkyl'benzenesulfonate being about 3:1 to
  • the said emulsifying agents providing about 9% to 20% of the Weight of the solution, and the percentage of the said 1,1-bis(chlorophenyl)-2,2,2-
  • a miticidal composition comprising a solution of 1, 'l-bis (chlorophenyl -2,2,2-t-richloroethanol and emulsifying agents in methyl oleate, the ratio of said 1,1-bis- (ch lorophenyl)-2,2,2-trichloroethanol to methyl oleate being from 1:2 to 1:1 and the emulsifying agents consisting of an alkylphenoxypo lyethoxyethanol having 20 to other units and containing 8 to 12 carbon atoms in its alltyl substituent and a surface active, oil-soluble calcium alkylbenzenesulfonate wherein the alkyl substituent contains from 8 to 18 carbon atoms, the ratio of the ialkylphenoxypolyethoxyethanol to the calcium aikylbenzenesulfonate being about 3:1 to about 1:1 byweight, the said emulsifying agent providing about 9% to 20% of the weight of the solution.
  • composition according to claim 11 in which the a1kylphenoxypolyethoxyethanol is diisobutylphenoxypolyethoxyethanol.
  • a composition according to claim 11 in which the calcium alkylbenzenesulfonate is calcium dodecylbenzenesu'lfonate.
  • a miticid al composition comprising :a solution of about 50% by weight of 1,l-bis(chlorophenyl)-2,2,2-trichloroethanol and 10% by weight of emulsifying agents in methyloleate, the emulsifying agents consisting of pdiisobutylphenoxypolyethoxyethano1 containing about 30 ether groups and calcium dodecylbenzenesulfonate in about equal weights.
  • a miticidal composition comprising about 50% by weight of a finely divided hydrated silica carrying about an equal weight of a solution of about 50 parts by weight of '1,l-bis(chlorophenyl)-2,2,24trichloroethano1 and 10 parts by weight of emulsifying agents dissolved in 40 parts by weight of methyl oleate, the emulsifying agents consisting of p-diisobutylphenoxypolyethoxyethanol containing about 30 ether groups and calcium dodecylbenzenesulfonate in about equal weights.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US109505A 1961-05-12 1961-05-12 Miticidal compositions Expired - Lifetime US3102070A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US109505A US3102070A (en) 1961-05-12 1961-05-12 Miticidal compositions
BR138794/62A BR6238794D0 (pt) 1961-05-12 1962-05-04 Composicoes miticidas
GB17529/62A GB995383A (en) 1961-05-12 1962-05-07 Miticidal containing 1,1-bis(halophenyl)-2,2,2-tri-chloroethanols
ES277137A ES277137A1 (es) 1961-05-12 1962-05-08 Un procedimiento para preparar un agente mitricida en forma de concentrado de emulsión o polvo hemectable
CH572862A CH409513A (fr) 1961-05-12 1962-05-11 Nouvelle composition acaricide
AT390062A AT246491B (de) 1961-05-12 1962-05-11 Milbenbekämfungsmittel
MY196984A MY6900084A (en) 1961-05-12 1969-12-31 Miticidal containing 1,1,-bis (halophenyl) -2,2,2-tri-chloro-ethanols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US109505A US3102070A (en) 1961-05-12 1961-05-12 Miticidal compositions

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US3102070A true US3102070A (en) 1963-08-27

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US109505A Expired - Lifetime US3102070A (en) 1961-05-12 1961-05-12 Miticidal compositions

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US (1) US3102070A (fr)
AT (1) AT246491B (fr)
BR (1) BR6238794D0 (fr)
CH (1) CH409513A (fr)
ES (1) ES277137A1 (fr)
GB (1) GB995383A (fr)
MY (1) MY6900084A (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3256201A (en) * 1955-09-27 1966-06-14 Armour & Co Antiseptic detergent compositions
US3442818A (en) * 1965-03-12 1969-05-06 Swift & Co Emulsifiers for agricultural pesticides
US4357350A (en) * 1978-05-17 1982-11-02 Roussel Uclaf Novel acaricide compositions
US4705902A (en) * 1985-10-03 1987-11-10 Rohm And Haas Company DDTR-free 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2677849B1 (fr) * 1991-06-20 1995-06-16 Francais Prod Ind Cfpi Poudres mouillables phytopharmaceutiques et leur procede de preparation.
JP3855321B2 (ja) * 1996-11-01 2006-12-06 住友化学株式会社 農薬組成物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2696453A (en) * 1952-05-27 1954-12-07 Herbert L Sanders Emulsifiers and toxicants containing the same
US2812280A (en) * 1954-04-20 1957-11-05 Rohm & Haas Preparation of bis (halophenyl) trichloroethanol
US2819996A (en) * 1955-11-23 1958-01-14 Rohm & Haas Stabilized pesticidal emulsifier composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2696453A (en) * 1952-05-27 1954-12-07 Herbert L Sanders Emulsifiers and toxicants containing the same
US2812280A (en) * 1954-04-20 1957-11-05 Rohm & Haas Preparation of bis (halophenyl) trichloroethanol
US2819996A (en) * 1955-11-23 1958-01-14 Rohm & Haas Stabilized pesticidal emulsifier composition

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3256201A (en) * 1955-09-27 1966-06-14 Armour & Co Antiseptic detergent compositions
US3442818A (en) * 1965-03-12 1969-05-06 Swift & Co Emulsifiers for agricultural pesticides
US4357350A (en) * 1978-05-17 1982-11-02 Roussel Uclaf Novel acaricide compositions
US4705902A (en) * 1985-10-03 1987-11-10 Rohm And Haas Company DDTR-free 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol

Also Published As

Publication number Publication date
ES277137A1 (es) 1962-09-16
CH409513A (fr) 1966-03-15
GB995383A (en) 1965-06-16
MY6900084A (en) 1969-12-31
AT246491B (de) 1966-04-25
BR6238794D0 (pt) 1973-05-10

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