Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
  • C07D339/08—Six-membered rings

Definitions

• R, R R and'R are substituents such as alkyl.
• the compounds are useful insecticides.
• the present invention relates to sulphur containing heterocyclic compounds and more specifically to amino-l,3-dithiane derivatives possessing insecticidal properties.
• R is alkyl of l to 5 carbon atoms
• R is hydrogen or alkyl or I to 5 carbon atoms
• R and R are each, independently, alkyl of l to 5 carbon atoms, or
• R, R R and R are alkyl of over 2 carbon atoms, this may be branched or straight chain, a primary or secondary alkyl and when of over 3 carbon atoms, the alkyl may be tertiary :alkyl.
• this is preferably of l, 2, 3 or 4 carbon atoms, e.g. methyl, ethyl, npropyl, n-butyl or sec.butytl.
• R and R together with the nitrogen atom to which they are bound, form a 5 to 6 membered heterocyclic ring, this preferably contains one nitrogen hetero atom, two nitrogen hetero atoms or one nitrogen hetero atom and one oxygen hetero atom.
• lieterocyclic rings formed by R, and R together with the nitrogen atom to which they are bound are pipcridino, pyrrolidino, piperazino and morpholino, particularly the 6 membered heterocyclic rings.
• the compounds of formula I may exist in either free base or acid addition salt form.
• Acid addition salt forms may be produced from free base forms in manner known per se and vice versa.
• the process of the invention may, for example, be effected as follows viz:
• a compound of formula II is conveniently reacted with stirring, with a compound of formula Ill, over a period of 2 to 6 hours, e.g. 3 hours, in an appropiate anhydrous solvent, such as a nitrile, e.g. acetonitrile.
• An acid acceptor e.g. triethylamine is preferably employed, especially if the compound of formula ll is employed in acid addition salt form, in which case, an excess of acid acceptor is preferably employed.
• the compounds of formula ll, employed as starting material in the process of the present invention may, for example, be produced by condensing a compound of formula IV,
• the reaction may be effected by dissolving a compound of formula IV in a solvent suchas chloroform, in an inert atmosphere such as nitrogen, and passing the chlorocyane through the solution at a slightly elevated temperature, e.g. between 40 and 50C over a period of between 4 and 8 hours, e.g. 5 to 6 hours, preferably with stirring.
• a solvent such as chloroform
• an inert atmosphere such as nitrogen
• Working up may be effected in conventional manner.
• the compounds possess low toxicity in warm blooded animals as indicated by LD determinations on male white rats.
• the compounds are therefore useful as insecticides particularly in animal buildings e.g. stables, in houses e.g. in cellars and attics thereof, and in plant loci.
• the amount of the compound to be applied will vary depending on the particular compound employed, the mode of application, am-
• an indicated amount to be applied to a plant locus is between 200g and 5 Kg/hectare.
• the compounds may be employed as a composition with insecticidal or fungicidal carriers and diluents in solid or liquid form e.g. spraying and dusting powders, strewing granulates, spraying liquids and aerosols.
• Solid forms may include diluents and carriers such as diatomaceous earth, talc, koalinite, attapulgite, pyrophyllite, artifical mineral fillers based on SiO and silicates, limestone, decahydrate and plant material carriers such as walnut and flour.
• Adjuvants e.g. surfactants such'as wetting and dispersing agents, e.g. sodium lauryl sulphate, sodium dodecyl benzenesulphonate, condensation products from naphthalene sulphonate and formaldehyde, polyglycol ether and lignin derivatives such as sulphite liquor, may also be included in the case of wettable powders to be applied as a water suspension.
• Granulates are produced by coating or impregnating granular carrier materials such as pumice, limestone, attapulgite and koalinite with the compounds.
• Liquid forms may include non-phytotoxic diluents and carriers such as alcohols, glycolic ethers, aliphatic and aromatic hydrocarbons e.g. xylene, alkyl naphthalenes and other petroleum distillates, and ketones e.g. cyclohexanone and isophorone.
• Adjuvants such as surface active agents, e.g. wetting and emulsifying agents such as polyglycol ether formed by the reaction of an alkylene oxide with high molecular weight alcohols, mercaptans or alkyl phenols, and/or alkyl benzene sulphonates, may be included in emulsion concentrate forms.
• adjuvants such as stabilizing agents, desactivators (for solid forms with carriers having an active surface), agents for improving adhesiveness to surfaces treated, anticorrosives, defoaming agents and pigments may also be included.
• Concentrate forms of composition generally contain between i and 5 percent preferably between 5 and 50 percent by weight of active compound.
• compositions generally contain between 0.01 and 95 percent, preferably between 0.01 and percent by weight of active compound.
• Emulsifiable concentrate 25 parts by weight of an active agent of formula I, 5 parts by weight of a condensation product form formaldehyde and naphthalene sulphonate, 2 parts by weight of dextrin, 1 part by weight of ammonium caseinate and 62 parts byv weight of diatomaceous earth are mixed until a homogeneous mixture is obtained, and this is then ground until the particles are considerably smaller and 45 microns as an average. Before application the powder is diluted with water to the desired concentration.
• Emulsifiable concentrate 50 parts by weight of a compound of formula I are mixed with 50 parts by weight of sodium-lauryl sulphate, 3 parts by weight of sodium-lignine sulphonate and 45 parts by weight of kaolinite. The concentrate is diluted with water to the desired concentration before application.
• Free base and acid addition salt forms of the compounds of formula 1 exhibit the same order of activity.
• Examples of agriculturally acceptable acid addition salt forms are the acetates, benzoates, hydrogen oxalates, hydrochlorides and hydrogen sulphates.
• a preferred group of compounds of formula I are the compounds wherein R,, R R and R of formula I are each alkyl of l to 4 carbon atoms.
• R, and R of formula I are each alkyl, and R and R, together with the nitrogen atom to which they are bound form a piperidino, piperazino or a morpholino heterocyclic ring, especially a piperidino ring.
• R, and R are each independently, alkyl of l to carbon atoms.
• R and R are each independently alkyl of l to 5 carbon atoms.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Heterocyclic Compounds Containing Sulfur Atoms (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

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Publications (1)

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Country Status (8)

Cited By (1)

Citations (3)

• 1973
  • 1973-07-30 US US383823A patent/US3878216A/en not_active Expired - Lifetime
  • 1973-08-03 IT IT51835/73A patent/IT990139B/it active
  • 1973-08-10 BR BR6123/73A patent/BR7306123D0/pt unknown
  • 1973-08-13 IL IL42960A patent/IL42960A0/xx unknown
  • 1973-08-13 FR FR7329487A patent/FR2196337B3/fr not_active Expired
  • 1973-08-13 DE DE19732340925 patent/DE2340925A1/de active Pending
  • 1973-08-15 JP JP48091614A patent/JPS49124227A/ja active Pending
  • 1973-08-15 ZA ZA00735586A patent/ZA735586B/xx unknown

Patent Citations (3)

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