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United States Patent Office Patented June 7, 1966 1 3,255,075 United States Patent Office Patented June 7, 1966 1. 2 ethylene thioethers and long chain quaternary ammonium 3,255,075 chloride compounds. METHANETHOL CONTAINING NEMATOCEDES Max J. Fielding, Wilmington, Del, assignor to E. I. du Surface-active dispersing agents such as sodium lignin Pont de Nemours and Company, Wilmington, Del, a sulfonates, low viscosity methyl cellulose and polymerized corporation of Delaware sodium salts of alkyl naphthalene sulfonic acids are also No Drawing. Filed Mar. 29, 1963, Ser. No. 269,143 suitable in the nematocidal compositions of this invention. 3 Claims. (Cl. 167-22) Among the more preferred surfactants are the anionic and non-ionic types. Among the anionic surface-active This invention relates to nematocidal compositions and agents, preferred ones are alkali metal or amine salts of methods. 10 alkyl benzene sulfonic acids, such as dodecylbenzene More specifically, this invention refers to a method of sulfonic acid, sodium lauryl sulfate, alkyl naphthalene sul killing plant pathogenic nematodes by applying to said fonates, sodium N-methyl-N-oleoyltaurate, oleic acid ester. nematodes a mercapto-terminated thiomethylene com of sodium isethionate, dioctyl sodium sulfosuccinate and pound. sodium dodecyldiphenyloxide disulfonate. Among the Plant nematodes are found in virtually all soils in which 5 non-ionic compounds, preferred members are alkyl phen plants will grow. Consequently, every major crop is a oxy poly(ethyleneoxy)ethanols such as nonyl phenol ad potential victim of this pest. The annual toll on crops ducts with ethylene oxide; also preferred are trimethyl in the United States is well over several hundred million nonyl polyethylene glycol ethers, polyethylene oxide ad dollars. A practical commercial chemical is needed to ducts of fatty and rosin acids, long chain alkyl mercaptan stop this unnecessary loss. However, in order to be com 20 adducts with ethylene oxide and polyethylene oxide ad mercially practicable a chemical must be non-toxic to ducts with sorbitan fatty acid esters. animals and plants and kill a broad spectrum of nematodes In general, less than 10% by weight of the surface at low rates. active agent will be used in compositions of this invention I have discovered that the following compounds qualify and ordinarily the amount of surface-active agents will as effective commercial nematocides: 25 range from 0.5 to 5% by weight. Nematocidal compositions of this invention can also Methanedithiol, contain finely divided inert diluents, such as talcs, natural Thiodi(methanethiol), clays, including attapulgite clay and kaolinite clay, pyro Methylenedithiobis(methanethiol), and phyllite, diatomaceous earths, synthetic fine silicas, cal Thiodimethylenedithiobis(methanethiol). 30 cium silicate, carbonates, calcium phosphates, lime, and Although all of the above compounds kill nematodes, such flours as walnut shell, wheat, redwood, soybean and particularly outstanding results are obtained from thiodi cottonseed flour. (methanethiol), methylenedithiobis(methanethiol) and The amount of the finely divided inert solid diluent thiodimethylenedithiobis(methanethiol). can vary widely but will generally range from 1 to 50% The most highly preferred compound because of its out by weight of the nematocidal composition. Compositions standing activity at low rates is thiodi(methanethiol). of from 2 to 30% active ingredient are preferred. The Acceptable nematocidal treatments are obtained from particle size can vary considerably but will ordinarily be a mixture of two or more of all the above compounds. somewhat under 50 microns in the finished formulation. A preferred formulation contains from about 10 to 50% PREPARATION 40 by weight of a mercapto-terminated thiomethylene, a total Methanedithiol is prepared in the manner described by of 45 to 89% by weight of solid diluents and 1 to 5% Cairns et al., J. Am. Chem. Soc., 74, 3982 (1952). by weight of one or more surfactants. Thiodimethanethiol is formed along with methanedithiol Although the compounds used in this invention are in the reaction between hydrogen sulfide and formalde normally liquids, it is possible to formulate them into hyde and may be separated by distillation. Methylenedi dusts for direct application or into wettable powders which thiolbis(methanethiol) and thiodimethylenedithiobis are applied in a slurry. In the case of wettable powders, (methanethiol) are prepared by the process described in surfactants and diluents are usually both present in the Saegebarth, U.S. Patent 3,056,841. nematocidal composition. COMPOSITION It is sometimes also advantageous to formulate the 50 nematocidal compound of this invention as granules or Compositions of this invention comprise one or more pellets, for example by applying the active ingredient to of the compounds described above together with one or preformed clay granules, such as granular attapulgite, or more surface-active agents. to granular vermiculite. Usually, such granules will con The surface-active agents used in this invention can be tain 1 to 10% by weight of the active ingredient, although a wetting, dispersing or an emulsifying agent which will for special uses as much as 15 to 20% by weight can be assist dispersion of the compound. Surface-active agents applied. or surfactants can include such anionic, cationic and non Emulsifiable oil solutions can be employed with one ionic agents as have heretofore been generally employed or more of the mercapto-terminated thiomethylenes used in plant control compositions of similar type. Suitable in this invention. In these nematocidal compositions, the surface-active agents are set out, for example, in Searle 60 surface-active agent and the oil form a liquid which can U.S. Patent 2,426,417; Todd U.S. Patent 2,655,417; Jones be conveniently poured and measured. Such solutions can U.S. Patent 2,412,510; or Leniher U.S. Patent 2,139,276. be mixed with water at the point of application to form A detailed list of such agents is set forth in "Detergents an emulsion containing the nematocide and the solvent. and Emulsifiers-Up to Date' (1962) by John W. Mc Such compositions have the advantage that the oil will Cutcheon, Inc., and Bulletin E-607 of the Bureau of En 65 often act as a foam inhibitor and thus reduce the tendency tomology and Plant Quarantine of the U.S. Department of for large amounts of surfactants to form objectionable Agriculture. foam. The oil used such as toluene, kerosene, stoddard Suitable surface-active agents for use in compositions of solvent, xylene, alkylated naphthalene, diesel oil and the the present invention are: polyethylene glycol fatty esters. like should be preferably water immiscible and be of a and fatty alkylol amide condensates, alkyl aryl Sulfonates, 70 type in which the active agent will be soluble in the fatty alcohol sulfates, dialkyl esters of sodium sulfosuc amounts used in particular formulations. Other solvents, cinate, fatty acid esters of sodium isethionate, polyoxy such as chlorinated hydrocarbons like tetrachloroethylene, 3,255,075 3 4. ketones like cyclohexanones, celloSolves, N,N-dialkyl Methyl mercury nitrile; amides, carbitols, and the like can also be used, either Tetrachloroquinone; and alone or in admixture with the hydrocarbon Solvents N-trichloromethylthiophthalimide. shown above. The above fungicides are added to compositions con In the above emulsifiable oil concentrates, the mer taining a mercapto-terminated thiomethylene at the rate capto-terminated thiomethylenes will be present in of 1 to 400 pounds to each 20 pounds of a compound amounts ranging from 5 to 80% by weight, 10 to 35% within the scope of this invention. Illustrative of fungi by weight being a preferred range. Precise concentrations cides used at low rates with the mercapto-terminated thio of active agent, of course, will depend on the intended use methylenes are the above-described organo mercurials. of the composition. When mixed with water at the O Illustrative of fungicides used at high rates with the mer point of application the oil concentrate will be diluted so capto-terminated thiomethylenes are thiuram sulfides and that in the final spray emulsion the active agent will be captan. Of course, more or less of the above-listed fungi present in amounts ranging from 0.5 to 2% by weight. cides can be added to a composition of this invention de A formulation that I have found to be especially advan pending on the fungi present in the area to be protected. tageous in the application of mercapto-terminated thio 5 Compositions of this invention can additionally con methylenes to nematode infested soil is a composition tain soil insecticides such as chlordane, DDT, dieldrin, containing from about 20 to 80% by weight of mercapto endrin, aldrin, methoxychlor and others for simultaneous terminated thiomethylenes, from about 17 to 75% by application of nematocide, fungicide and insecticide to weight of one or more inert liquid diluents and from the soil. about 0.5 to 8% by weight of one or more surface-active 20 In addition compositions can contain special additives agents. such as corrosion inhibitors, pigments, antifoam agents and the like. APPLICATION The compounds used in this invention can also be ap plied, mixed or in common solution with other chemicals As a practical matter application rates of from 2 to 25 which are used in agronomic and horticultural manage 100 pounds of active mercapto-terminated thiomethylenes ment and are compatible with the compounds used in this per treated acre of soil are satisfactory for nematode invention. Such chemicals can be but are not restricted control, although higher rates can be used. The active to the classes of chemicals commonly known as plant nu mercapto-terminated thiomethylene, preferably in a Suit. trients, fertilizers, herbicides and other nematocides. able formulation as described above is applied to the Soil 30 by any conventional method such as spraying or dusting The following additional examples in which all percents by hand or mechanical equipment. After application, the unless otherwise indicated are by weight are provided to composition is worked into the ground to a depth of about more clearly explain this invention.
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