US3878216A - 2-Sulphenylimino-5-amino-1,3-dithianes - Google Patents

2-Sulphenylimino-5-amino-1,3-dithianes Download PDF

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Publication number
US3878216A
US3878216A US383823A US38382373A US3878216A US 3878216 A US3878216 A US 3878216A US 383823 A US383823 A US 383823A US 38382373 A US38382373 A US 38382373A US 3878216 A US3878216 A US 3878216A
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US
United States
Prior art keywords
compound
dithiane
formula
alkyl
dimethylamino
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
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US383823A
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English (en)
Inventor
Rupert Schneider
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Sandoz AG
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Sandoz AG
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Filing date
Publication date
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Publication of US3878216A publication Critical patent/US3878216A/en
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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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
US383823A 1972-08-15 1973-07-30 2-Sulphenylimino-5-amino-1,3-dithianes Expired - Lifetime US3878216A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1205672 1972-08-15

Publications (1)

Publication Number Publication Date
US3878216A true US3878216A (en) 1975-04-15

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ID=4379431

Family Applications (1)

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US383823A Expired - Lifetime US3878216A (en) 1972-08-15 1973-07-30 2-Sulphenylimino-5-amino-1,3-dithianes

Country Status (8)

Country Link
US (1) US3878216A (sv)
JP (1) JPS49124227A (sv)
BR (1) BR7306123D0 (sv)
DE (1) DE2340925A1 (sv)
FR (1) FR2196337B3 (sv)
IL (1) IL42960A0 (sv)
IT (1) IT990139B (sv)
ZA (1) ZA735586B (sv)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5502073A (en) * 1987-06-05 1996-03-26 The Wellcome Foundation Heterocyclic pesticidal compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3322788A (en) * 1962-09-14 1967-05-30 Bayer Ag Sulphonylimino-dithiocarbonic acid esters and a process for their production
US3389148A (en) * 1966-08-31 1968-06-18 American Cyanamid Co Processes for the preparation of ringsubstituted 2-imino-1, 3-dithioheterocycle compounds
US3770769A (en) * 1970-09-29 1973-11-06 Sandoz Ltd 2-imino-5-alkylamino-1,3-dithianes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3322788A (en) * 1962-09-14 1967-05-30 Bayer Ag Sulphonylimino-dithiocarbonic acid esters and a process for their production
US3389148A (en) * 1966-08-31 1968-06-18 American Cyanamid Co Processes for the preparation of ringsubstituted 2-imino-1, 3-dithioheterocycle compounds
US3770769A (en) * 1970-09-29 1973-11-06 Sandoz Ltd 2-imino-5-alkylamino-1,3-dithianes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5502073A (en) * 1987-06-05 1996-03-26 The Wellcome Foundation Heterocyclic pesticidal compounds

Also Published As

Publication number Publication date
DE2340925A1 (de) 1974-04-04
FR2196337B3 (sv) 1976-07-23
ZA735586B (en) 1975-04-30
JPS49124227A (sv) 1974-11-28
FR2196337A1 (sv) 1974-03-15
BR7306123D0 (pt) 1974-06-27
IL42960A0 (en) 1973-11-28
IT990139B (it) 1975-06-20

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