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United States Patent (19) (11) Patent Number: 4,994,261 Scher Et Al

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United States Patent (19) (11) Patent Number: 4,994,261 Scher Et Al United States Patent (19) (11) Patent Number: 4,994,261 Scher et al. 45) Date of Patent: Feb. 19, 1991 (54) PESTCDE COMPOST ONS AND (56) References Cited METHOD U.S. PATENT DOCUMENTS 2,988,474 6/196l Szabo et al. ......................... 54/141 (75) Inventors: Herbert B. Scher, Moraga; Marius 3,959,464 5/1976 DeSavigny. ... 424/78 Rodson, El Cerrito; Ronald L. 4,140,516 2/1979 Scher .. 71/88 Morgan, Daly City, all of Calif. 4,285,720 8/1981 Scher ...................................... 71/88 (73) Assignee: ICI Americas Inc., Wilmington, Del. FOREIGN PATENT DOCUMENTS 0.134674 9/1988 European Pat. Off. ............ 514/14 (21) Appl. No.: 232,193 Primary Examiner-Allen J. Robinson Attorney, Agent, or Firm-Denis A. Polyn 22 Filed: Aug. 15, 1988 57) ABSTRACT Toxicant, especially pesticide compositions, having Related U.S. Application Data lowered dermal toxicity are provided. The composi. (63) Continuation of Ser. No. 846,183, Mar. 31, 1986, aban tions include a lipophilic-pesticide, a nonionic surfac doned. tant and a dry inert diluent carrier. Methods for reduc ing the dermal toxicity of lipophilic toxicants, especially (51) Int. Cl. ............................................. A01N 57/18 pesticides are provided, as well as methods for control (52) U.S. C. ...................................... 424/10; 514/141; ling insect pests using the disclosed compositions. 514/974 (58) Field of Search ................... 424/10; 514/141, 974 12 Claims, No Drawings 4,994,261 1. 2 serve the pesticidal effectiveness of the compounds as PESTICIDE COMPOSITIONS AND METHOD applied to the pest or the locus where the pest may be found. This is a continuation of application Ser. No. 846,183, filed Mar. 31, 1986, now abandoned. SUMMARY OF THE INVENTION There has now been discovered a pesticidal composi FIELD OF THE INVENTION tion that maintains high biological effectiveness against The invention relates to dermally toxic pesticide pests when used in the field and has reduced dermal compositions consisting of the pesticide and a dry, inert toxicity. diluent carrier, that have been additionally safened for 10 The compositions comprise a biologically effective handling by addition thereto of a nonionic surfactant amount of a dermally toxic pesticide, a nonionic surfac having an HLB of from about 17 to about 20. tant having an HLB of from about 17 to about 20 and a dry inert diluent carrier. BACKGROUND OF THE INVENTION More particularly, the compositions comprise A wide variety of pesticides are commonly used in 15 (a) a biologically effective amount of a dermally toxic agronomic and horticultural pursuits. As used herein pesticide; the term "pesticide' means any chemical compound or (b) a dinonyl phenol ethoxylate surfactant; and composition which displays biological activity in an (c) a dry inert diluent clay carrier, in granular form. agricultural field site or at any locus where control of Dermal toxicity includes systemic toxic effects that biological growth is desired. The biological activity or 20 occur in an animal or human as a result of dermal control contemplated herein includes all forms of contact with a toxic substance for a defined period of growth modification, ranging from regulation and re time. Dermal toxicity may be defined as the LD-50 tardation to killing, and extends to all forms of plant and (lethal dose to 50% of the animals in a test group) animal life found in an agricultural environment during caused by a 24 hour exposure to a toxic substance. some time during the pest's life cycle. Pesticides within 25 this invention include anti-foulants, plant growth regu Pesticides of the composition disclosed herein include lants, soil fumigants, molluscicides, insecticides, herbi dermally toxic organophosphorus, pyrethroids, phos cides, fungicides, rodenticides, nematocides, algicides, phonate and thiophosphonate compounds. The follow predator control agents, and insect and animal repel ing are examples of such compounds, followed in paren lents. Additional biologically active compounds can 30 thesis by their common names, where available: also be present in admixture with the primary ingredi S-tert-butylthiomethyl O,O-diethyl phosphorodithioate ent, such as synergists, antidotes, fertilizers, soil life (terbufos) extenders, and additional pesticides. O,O-diethyl-O-4-methylsulphinylphenyl phosphorothi The term "biologically effective amount' is used oate (fensulfothion) herein to denote any quantity of pesticide or pesticide 35 O,O-diethyl O-2-isopropyl-6-methylpyridimidin-4-yl composition, which when applied to an agricultural site phosphorothioate (diazinon) in any conventional manner causes the occurrence of O,O-diethyl S-2-ethylthioethyl phosphorodithioate (di one or more of the biological effects mentioned above. sulfoton) As further explained in the latter portion of this specifi S-chloromethyl O,O-diethyl phosphorodithioate cation, the quantity of pesticide applied in a given situa 40 (chlormephos) tion depend on the pesticide itself, on the type of biolog O-ethyl S,S-dipropyl phosphorodithioate (ethopro ical activity inherent in the pesticide, and the degree of phos) such activity sought to be achieved. The selection of the O,O-diethyl S-ethylthiomethyl phosphorodithioate proper quantity to be applied, however, is within the (phorate) expertise of one skilled in the art. 45 O-(4-bromo-2-chlorophenyl) O-ethyl S-propyl phos Some pesticides, such as the chlorinated hydrocarbon phorodithioate (prophenofos) carbamate insecticides and the organophosphorus pesti S-1,2-di(ethoxycarbonyl)ethyl O,O-dimethyl phos cide compounds, including phosphonate, organophos phorodithioate (malathion) phate and organothiophosphate compounds present a O,O,O',O'-tetraethyl S,S'-methylene di(phosphorodi problem of dermal toxicity to persons handling these 50 thioate) (ethion) substances. O-(4-bromo-2,5-dichlorophenyl) O,O-diethyl phos If handled carelessly, improperly or in disregard of phorothioate (bromophos-ethyl) directions, the pesticide, depending upon its toxicity, S-4-chlorophenylthiomethyl O,O-diethyl phosphorodi may present a hazard to those handling the pesticide thioate (carbophenothion) whether in packaging it for sale, handling it for ship 55 2-chloro-1-(2,4-dichlorophenyl) vinyl diethyl phosphate ment, mixing it for field application or applying it in the (chlorphenvinphos) field. The toxicity of the pesticide will vary depending O-2,5-dichloro-4-(methylthio) phenyl O,O-diethyl upon a number of factors, including the inherent toxic phosphorodithioate (chlorthiophos) ity of the pesticide substance at its site of biological O-4-cyanophenyl O,O-dimethyl phosphorothioate action. Various physical properties of the pesticide in (cyanophos) cluding the hydrophilic-lipophilic balance of the pesti O,O-dimethyl O-2-methylthioethyl phosphorothioate cide affect the adsorption to and absorption by various (demiphion) tissues of the person handling the pesticide compound, O,O-diethyl O-2-ethylthioethyl phosphorothioate and thus affect the toxicity of the compound to the (demeton) person handling it. 65 O-2,4-dichlorophenyl O,O-diethyl phosphorothioate Thus, it is desirable to develop formulations for these (dichlorofenthion) pesticide compounds that reduce the dermal toxicity of O-2,4-dichlorophenyl O-ethyl phenylphosphonothioate the compounds to persons handling them yet still pre (EPBP) 4,994,261 3 4. O,O-diethyl O-5-phenylisoxazol-3-yl phosphorothioate R X (isoxathion) Nil 1,3-di(methoxycarbonyl)-1-propen-2-yl dimethyl phos P-R phate / 1,4-dioxan-2,3-diyl S,S-di(o,O-diethyl phosphorothioate R (dioxathion) O,O-dimethyl-O-4-nitro-m-tolyl phosphorothioate in which X is oxygen or sulfur; and R, R and R2 are (fenitrothion) independently selected from the group consisting of O,O-dimethyl O-4-methylthio-m-tolyl phosphorothio C1-C5 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C2-C6 ate (fenthion) 10 alkenyl, C2-C6 alkenoxy, C2-C6 alkenylthio, phenyl, O-(5-chloro-1-isopropyl-1,2,4-triazol-3-yl) O,O-diethyl phenoxy, phenylthio, C7-C9 phenylalkyl, C7-C9 pheny phosphorothioate (isazophos) lalkoxy, and C7-C9 phenylalkylthio, each member of S-2-isopropylthioethyl O,O-dimethyl phosphorodithio such group optionally substituted with up to three sub ate (isothioate) stituents selected from halogen, C1-C4 alkyl, C1-C4 4-(methylthio)phenyl dipropyl phosphate (propaphos) 15 alkoxy, cyano, and nitro. 1,2-dibromo-2,2-dichloroethyl dimethyl phosphate (na The terms "alkyl,” "alkoxy," etc., are intended to include both straight-chain and branched-chain groups, led) and all carbon atoms ranges are inclusive. More pre O,O-diethyl al-cyanobenzylideneamino-oxyphosphono ferred organophosphorus compounds are those in thioate (phoxim) 20 which X is sulfur, and R, R and R2 are independently O,O-diethyl O-4-nitrophenyl phosphorothioate (para C1-C4 alkoxy or phenoxy, the phenyl ring optionally thion) substituted with up to three groups selected from O-2-diethylamino-6-methylpyrimidin-4-yl O,O-diethyl C1-C3 alkyl, nitro, cyano, and halogen. Highly pre phosphorothioate (piriniphos-ethyl) ferred are those in which X is sulfur, R is C1-C4 alkoxy, O-2-diethylamino-6-methylpyrimidin-4-yl 25 R1 is C1-C4 alkoxy, and R2 is phenoxy substituted with dimethyl phosphorothioate (pirimiphos-methyl) up to three substituents selected from C1-C3 alkyl and O,O,O',O'-tetraethyldithiopyrophosphate (sulfotep) nitro. O,O,O',O'-tetramethyl O,O'-thiodi-p-phenylene diphos Specific preferred pesticide compounds include S phorothioate (ternephos) tert-butylthiomethyl-O,O-diethylphosphorodithioate S-2-ethylthioethyl
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