Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D277/54—Nitrogen and either oxygen or sulfur atoms
• • 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
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
  • C07C335/04—Derivatives of thiourea
  • C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
  • C07C335/28—Y being a hetero atom, e.g. thiobiuret

Definitions

• alkoxy and alkanoylamino radicals are useful as fungicides. 3,759,938 9/1973 Giraudon 260/306.7
• thiazolidine derivatives of the present invention are those of the general formula:
• R represents a lower alkyl radical
• R represents a hydrogen atom, a lower alkyl radical or a phenyl radical
• R represents a lower alkyl radical optionally substituted by one or more halogen atoms
• a phenyl radical optionally carrying one, two or three substituents selected from halogen atoms and lower alkyl, lower alkoxy and lower alkanoylamino radicals, or a naphthyl radical.
• R represents a phenyl radical carrying two or three substituents, the substituents may be the same or different.
• alkoxy and alkanoylamin'o radicals means that the radical contains at most four carbon atoms.
• the thiazolidine derivatives of general formula I are prepared by reacting a thiourea of the general formula:
• reaction is generally carried out in an organic solvent, e.g., acetone, and at a temperature between 0C. and the boiling point of the reaction mixture.
• organic solvent e.g., acetone
• the aniline derivatives of general formula V can be obtained by reaction of a sulphonyl chloride of the general formula:
• the thiazolidine derivatives of general formula I possess useful fungicidal properties; they have particularly interesting contact activity against cucumber mildew (Erysiphe cichoracearum), apple mildew (Podosphaera leucotricha), bean anthracnose (Collerotrichum lindemuthianum) and wheat rust (Puccinia glumarum) when applied at quantities of between 10 and 50 g. per heetolitre of liquid diluent. They furthermore have the advantage of being systemic, in particular when they are applied by sprinkling the soil with liquid compositions containing them, against bean anthracnose and against cucumber mildew at doses greater than or equal to 0.1 g./hectolitre.
• Preferred thiazolidine derivatives of general formula I are those wherein R represents a methyl or ethyl radical and R, represents a hydrogen atom, and especially those wherein the substituent NHSO -R (wherein R is as hereinbefore defined) is in the 2- position of the phenyl ring, and more particularly those such compounds wherein R represents a methyl radical.
• the starting materials of the general formula ll can be prepared by using the method described below for the preparation of l-methoxycarbonyl-3-(Z-phenylsulphonylamino-phenyl)-thiourea.
• Methyl chlororformate (22.2 g.) is added, with stirring, to a solution of potassium thiocyanate (24.4 g.) in acetone (200 cc.). The temperature of the reaction mixture rises gradually to 35C. The mixture is then heated at the reflux temperature for 30 minutes. After cooling, Z-phenylsulphonylamino-aniline (24.8 g.) is added over the course of a few minutes and without allowing the temperature to exceed 20C. The reaction is very slightly exothermic. The reaction mixture is stirred for 16 hours at'a temperature of about 20C. Water (200 cc.) is then added and the mixture is stirred for 1 hour at a temperatue of about 20C.
• compositions which contain, as the active ingredients, at least one thiazolidine derivative of general formula I in association with one or more diluents or adjuvants compatible with the thiazolidine derivative(s) and suitable for use in agricultural fungicidal compositions.
• These compositions can optionally contain other compatible pesticides, such as insecticides or fungicides (e.g., maneb).
• the compositions contain between 0.005 and percent by weight of thiazolidine derivative.
• compositions may be solid if there is employed a powdered solid compatible diluent such as talc, calcined magnesia, kie'selguhr, tricalcium phosphate, powdered cork, adsorbent charcoal, or a clay such as kaolin or bentonite.
• a powdered solid compatible diluent such as talc, calcined magnesia, kie'selguhr, tricalcium phosphate, powdered cork, adsorbent charcoal, or a clay such as kaolin or bentonite.
• These solid compositions are preferably prepared by grinding the thiazolidine derivative with the solid diluent, or by impregnating the solid diluent with a solution of the thiazolidine derivative in a volatile solvent, evaporating the solvent, and if necessary grinding the product so as to obtain a powder.
• compositions may take the form of suspensions, emulsions or solutions in organic or aqueous-organic media, for example aromatic hydrocarbons such as toluene or xylene, mineral, animal or vegetable oils, or acetophenone, or mixtures of these diluents.
• aromatic hydrocarbons such as toluene or xylene, mineral, animal or vegetable oils, or acetophenone, or mixtures of these diluents.
• compositions in the form of suspensions, emulsions or solutions may contain wetting, dispersing or emulsifying agents of the ionic or non-ionic type, for example sulphoricinoleates, quaternary ammonium derivatives or products based on condensates of ethylene oxide such as the condensates of ethylene oxide with octylphenol, or fatty acid esters of anhydrosorbitols which have been rendered soluble by etherification of the free hydroxyl groups by condensation with ethylene oxide. It is preferable to use agents of the non-ionic type because they are not sensitive to electrolytes.
• the thiazolidine derivatives may be EXAMPLE 3
• a wettable powder containing 50 percent by weight of active material and having the following composition is prepared in accordance with the usual technique:
• R represents alkyl of l to 4 carbon atoms
• R represents hydrogen, alkyl of l to 4 carbon atoms or phenyl.
• R represents alkyl of l to 4 carbon atoms, alkyl of l to 4 carbon atoms substituted by halogen, phenyl or phenyl carrying one, two or three substitucnts selected from the class consisting of halogen and alkyl.
• the thiazolidine derivative according to claim 1 which is 2-meth0Xycarbonylimino-3-(2- iodomethylsulphonylaminophenyl)-thiazolidin-4-one.
• the thiazolidine derivative according to claim 1 which is Z-methoxycarbonylimino-3-(2-2- naphthylsulphonylamino-phenyl)-thiazolidin-4-one.
• the thiazolidine derivative according to claim 1 which is 2-methoxycarbonylimino-3-(2-4- acetamidophenylsulphonylamino-phenyl)-thiazolidin- 4-one.
• the thiazolidine derivative according to claim 1 which is 2-methoxycarbonylimino-3-(2-4- methylphenylsulphonylamino-phenyl)-thiazolidin- 4-one.

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• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Environmental Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Plant Pathology (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Thiazole And Isothizaole Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Plural Heterocyclic Compounds (AREA)

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Citations (1)

• 0
  • BE BE793919D patent/BE793919A/xx unknown
• 1972
  • 1972-01-12 FR FR7200947A patent/FR2167307B1/fr not_active Expired
  • 1972-12-29 US US319877A patent/US3868382A/en not_active Expired - Lifetime
• 1973
  • 1973-01-04 NL NL7300134A patent/NL7300134A/xx unknown
  • 1973-01-10 JP JP48005359A patent/JPS4880733A/ja active Pending
  • 1973-01-10 GB GB140373A patent/GB1360365A/en not_active Expired
  • 1973-01-11 CH CH36673A patent/CH557834A/fr not_active IP Right Cessation
  • 1973-01-12 DE DE2301513A patent/DE2301513A1/de active Pending

Patent Citations (1)

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