Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C327/00—Thiocarboxylic acids
  • C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
• • 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

• This invention relates to substituted carbamates, preparation thereof and use thereof as insecticides for the control of pestiferous insects.
• U.S. Patent 3,576,834 issued April 27, 1971, relates to insecticidal compounds having the structure: such as methomyl.
• This invention relates to compounds of Formula I, their preparation, to insecticidal compositions containing them and to the method of using said compounds as insecticides.
• Specifically preferred for its outstanding insecticidal activity is dimethyl N,N'[[l,2-ethane- diylbis[thio(methylimino)carbonyloxy]]]bis(ethaneimidothioate).
• the compounds of Formula I can be prepared, as shown in Equation A, by reacting preferably at least two moles of a substituted N-(aminocarbonyloxy)-alkanimidothioic acid ester of Formula II with one mole of an alkane disulfenyl halide of Formula III in the presence of a base: wherein R, R 1 , and R 2 are as previously defined and X is halogen.
• the reaction can be carried out in any organic solvent which is inert to the reactants and the reaction products, e.g. methylene chloride, dioxane, tetrahydrofuran, chloroform, 1,2-dichlorethane, acetonitrile, benzene, toluene, the xylenes, acetone or methyl ethyl ketone. Mixtures of such solvents can also be used.
• a base which will function as an acid acceptor can be used in synthesizing the compounds of this invention.
• the process can be carried out at a temperature of between about -20° and 60°C, preferably between about -5° and 40°C. Pressure is not critical; for convenience, atmospheric pressure is preferred.
• Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few pints to several hundred gallons per acre. High strength compositions are primarily used as intermediates for further formulation.
• the formulations broadly, contain e.g. about 1% to 99% by weight of active ingredient(s) and at least one of (a) e.g. about 0% to 20% surfactant(s) and (b) e.g. about 1% to 99% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
• Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers," 2nd Edn., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts.
• Typical liquid diluents and solvents are described in Marsden, “Solvents Guide,” 2nd Edn., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C.
• compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques.
• the ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.
• the ingredients are blended, coarsely hammer milled and then air milled to produce particles of active ingredient essentially all below 10 microns in diameter.
• the product is reblended before packaging
• the ingredients are thoroughly blended.
• the liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
• the ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns.
• the ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns.
• the resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
• a slurry of wettable powder containing 50% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
• the ingredients are blended, hammer-milled and then moistened with about 12% water.
• the mixture is extruded as cylinders about 5 mm diameter which are cut to produce pellets about 3 mm long. These may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm opening).
• the granules held on a U.S.S. No. 40 sieve (0.42 mm opening) may be packaged for use and the fines recycled.
• the ingredients are blended and ground in a hammer mill to produce a high-strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm opening). This material may then be formulated in a variety of ways.
• the ingredients are thoroughly blended and packaged for use.
• the ingredients are combined and stirred to. produce a solution which can be emulsified in water for application.
• the ingredients are combined and stirred with gentle warming to speed solution.
• a fine screen filter is included in packaging operation to ensure the absence of any extraneous undissolved material in the product.
• the compounds of this invention are useful for control of insects which are detrimental to agriculture.
• insects controlled by the compounds of this invention include but are not limited to: cotton bollworm (Heliothis zea), tobacco budworm (Heliothis virescens), southern armyworm (Spodoptera eridania), beet armyworm (Spodoptera exigua), soybean looper (Pseudoplusia includens), Mexican bean beetle (Epilachna varivestis), and the house fly (Musca domestica).
• insects are controlled by applying the compound to the locus of infestation, to the area to be protected, or to the pests themselves.
• a compound of Formula I is generally applied to the foliage or other plant parts which are infested or which are to be protected. Effective amounts to be applied depend upon the species to be controlled, its life stage, its size and location, the amount of rainfall, the time of year, moisture, temperature, type of application, and other variables. In general, 0.1 to 10 kg/ha may be required for insect control in agriculture with rates of .2 to 4 kg/ha usually being sufficient in many situations. In large-scale field operations, rates in the range of 1/4 to 2 kg/ha are generally used.
• the compounds of this invention will generally be used in formulation with a carrier that commonly will contain oil or water. Applications may be made with ' concentrated or dilute suspensions of the insecticide in the carrier. Low-volume applications utilizing dispersions containing about 20% of the active ingredient may be preferred by some applicators while others may prefer dilute suspensions containing only 25 ppm in high-volume applications.
• the compounds of this invention possess significant advantages over prior art compounds, e.g fewer applications are required to provide a given level of insect control due to this distinctly longer residual insecticidal action. Use of fewer applications results in greater economy to the grower and dissemination of less insecticide in the environment. An additional advantage is lower phytotoxicity to cotton.
• the compounds will be incorporated into a formulation in a known manner with incorporation of other components such as (a) surfactants, (b) diluents, (c) additives to reduce foam or corrosion, or (d) preservatives to control microbiological growth.
• other components such as (a) surfactants, (b) diluents, (c) additives to reduce foam or corrosion, or (d) preservatives to control microbiological growth.
• the compounds of this invention can be mixed with fungicides, bactericides, acaricides, nematicides, other insecticides, or other biologically active compounds in order to achieve desired results with a minimum expenditure of time, effort and material. Amounts of these biologically active materials added for each part by weight of the composition of this invention may vary from 0.05 to 25 parts by weight. Suitable agents of this type are well-known to those skilled in the art. Some are listed below:
• the foliage only of red kidney bean plants in the two-leaf stage was sprayed to run-off with aqueous dispersions of dimethyl N,N'-[[1,2-ethanediylbis[thio-(methylimino)carbonyloxy]]]bis(ethanimidothioate) (I) at the dilutions indicated.
• the sprays contained Duponol L-144-WDG (sulfonated oleyl acetate surfactant) at a concentration of 1:3000.
• SAW southern armyworm
• Example 1 The plants from the test described in Example 1 were kept in a growth room at 77 ⁇ 2°F and 53 + 5% relative himidity for 7 days. At the end of that period of time the remaining cotyledonary leaf from each bean plant was placed singly in a Petri dish with southern armyworms as previously described. Insect mortality was again read 2 days later and is set forth below.
• Cotton plants approximately 22 cm in height having 3-4 true leaves were sprayed to run-off with an aqueous dispersion of dimethyl N,N'-[[1,2-ethane- diylbis[thio(methylimino)carbonyloxy]]]bis(ethanimi- dothioate) (I) at a concentration of 0.05%.
• the spray contained Duponol L-144-WDG at a concentration of 1:3000.
• Another set of plants was similarly treated with methomyl. Plant injury was evaluated 6 days after treatment and is recorded below.

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• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Dentistry (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Plant Pathology (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Applications Claiming Priority (4)

Publications (2)

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ID=27123592

Family Applications (1)

Country Status (22)

Cited By (1)

Citations (1)

• 1978
  • 1978-06-08 DK DK254378A patent/DK254378A/da not_active Application Discontinuation
  • 1978-06-23 PH PH21318A patent/PH13803A/en unknown
  • 1978-06-28 GB GB787828116A patent/GB2001628B/en not_active Expired
  • 1978-06-28 AU AU37526/78A patent/AU515983B2/en not_active Expired
  • 1978-06-28 TR TR19962A patent/TR19962A/xx unknown
  • 1978-06-28 MX MX787191U patent/MX5138E/es unknown
  • 1978-06-28 EP EP78300097A patent/EP0000283B1/de not_active Expired
  • 1978-06-28 EG EG406/78A patent/EG13741A/xx active
  • 1978-06-28 DE DE7878300097T patent/DE2861154D1/de not_active Expired
  • 1978-06-29 YU YU01541/78A patent/YU154178A/xx unknown
  • 1978-06-29 ES ES471280A patent/ES471280A1/es not_active Expired
  • 1978-06-29 CS CS784303A patent/CS199213B2/cs unknown
  • 1978-06-29 JP JP7812978A patent/JPS5444614A/ja active Pending
  • 1978-06-30 IE IE1324/78A patent/IE47205B1/en unknown
  • 1978-06-30 CA CA306,631A patent/CA1107292A/en not_active Expired
  • 1978-06-30 BR BR7804185A patent/BR7804185A/pt unknown
  • 1978-06-30 OA OA56548A patent/OA05999A/xx unknown
  • 1978-06-30 IL IL55050A patent/IL55050A/xx unknown
  • 1978-06-30 IT IT25229/78A patent/IT1158872B/it active
  • 1978-06-30 PL PL1978208044A patent/PL114208B1/pl unknown
  • 1978-06-30 GR GR56643A patent/GR64548B/el unknown
  • 1978-06-30 AR AR272767A patent/AR220138A1/es active

Patent Citations (1)

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