US3294874A - Omicron-alkyl-omicron-cycloalkyl-s-alkylthiolphosphoric acid esters - Google Patents

Omicron-alkyl-omicron-cycloalkyl-s-alkylthiolphosphoric acid esters Download PDF

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US3294874A
US3294874A US253070A US25307063A US3294874A US 3294874 A US3294874 A US 3294874A US 253070 A US253070 A US 253070A US 25307063 A US25307063 A US 25307063A US 3294874 A US3294874 A US 3294874A
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methyl
solutions
omicron
mol
aphids
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Schrader Gerhard
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Bayer AG
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Bayer AG
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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
    • H01R33/00—Coupling devices specially adapted for supporting apparatus and having one part acting as a holder providing support and electrical connection via a counterpart which is structurally associated with the apparatus, e.g. lamp holders; Separate parts thereof
    • H01R33/05—Two-pole devices
    • H01R33/06—Two-pole devices with two current-carrying pins, blades or analogous contacts, having their axes parallel to each other
    • H01R33/08—Two-pole devices with two current-carrying pins, blades or analogous contacts, having their axes parallel to each other for supporting tubular fluorescent lamp
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/1653—Esters of thiophosphoric acids with arylalkanols

Definitions

  • the present invention relates to and has as its objects new and useful insecticidally active phosphorus containing compounds. More specifically this invention is concerned with 0,0-dialkyland O-alkyl-O-cycloalkyl-S-alkylthiolphosphoric acid esters of the formula as Well as processes for the production of such compounds.
  • R stands for a secondary alkyl or a c-ycloalkyl radical
  • R denotes a linear preferably lower alkyl radical
  • R denotes an optionally substituted alkyl or aralkyl radical.
  • alkyl compounds are preferably used according to' the present invention which are known in the produc tion of effective insecticides based on phosphoric acid esters in which the two O-alkyl radicals are of primary character.
  • alkylor aryl mercaptoalkyl halides N-alkylor N,N-dialkylaminoalkyl halides, cyanalkyl halides, alkoxycarbonylalkyl halides, alkylmercaptocarbonylalkyl halides, N-alkylor N,N-dialkylaminocarbonylalkyl halides, aralkyl halides or the corresponding tosylates, and the like.
  • the new compounds very effectively kill insects like aphids, spider mites, caterpillars, flies etc. as well as nematodes. They distinguish themselves especially by a very good contact-insecticidal activity and mostly also by a systemic and ovicidal action.
  • inventive products are to be used as pest control agents, especially in plant protection. They may be used in the same manned as other known phosphoric insecticides, i.e. ina concentration from about 0.00001% to about 1% diluted or extended with suitable solid or liquid carriers or diluents.
  • Such solid carriers are talc, chalk, bentonite, clay and the like, as liquid carriers there may be mentioned water (if necessary with commercial emulsifiers), alcohols, especially lower alcohols such as methanol or ethanol, ketones, especially lower ketones such as acetone or methly ethyl ketone, liquid hydrocarbons and the like.
  • the new compounds may furthermore be used in combination with each other or with known insecticides, fertilizers etc.
  • inventive compounds of the following formulae have been tested against aphids (compounds I and II), spider mites (compounds I, H and III) and caterpillars (compounds I, II and III).
  • Aqueous dilutions of these compounds have been prepared by mixing the active ingredient-s with the same amounts of dimethyl formamide as an auxiliary solvent adding thereto 20% by weight referred to active ingredient of a commercial emulsifier consisting of a benzyl hydroxy polyglycol ether containing about to glycol ethers, and diluting this premixture at last with water to the desired concentration indicated in the following paragraphs:
  • Example 1 (a) sec. 041100 8 see. G4H O ⁇ fi P-ONH4 2 r-s-nn;
  • Spider mites are killed to 90% by 0.001% solutions and aphids are destroyed to 50% even by 0.0001% solutions of the ester. Moreover the compound shows an ovicidal activity against the eggs of spider mites.
  • Example 2 80 g. (0.4 mol) of O-methyl-O-sec.-butyl-thiophosphoric acid ammonium salt are dissolved in 250 cc. of acetonitrile. g. of chloromethyl thioethyl ether are added to this solution at to C. with stirring. Stirring is continued at the indicated temperature for one hour, and the reaction mixture is then worked up as described in Example 112. 72 g. (71% of the theoretical yield) of the O-methyl-O-sec.-butyl-S-(ethyl-mercap tomethyl)-thiolphosphoric acid ester of B.P. 81 C./0.01 mm. Hg are thus obtained.
  • the compound is a colourless water-insoluble oil.
  • Spider mites are completely destroyed by 0.01% solutions of the ester.
  • the systemic action of 0.1% solutions of the compound against aphids is Moreover the product possesses an ovicidal activity against the eggs of spider mites.
  • Insecticidal properties Yield (per- Structure cent of the theoretical) Concentra- Killingrate Physical properties Administration against tion of active of pests in substance percent sec. 04H0O O 1 -CN 57 B P 93 C /0 01mm H ⁇ Caterpillars 1001 80 2 Mosquito larvae 0.0001 100 CH3O see. C4H9O ⁇ (") /P--SCH2SC1 5 Not distillable Oil ⁇ g g fg 8'8 ⁇ 33 CHaO see. C4HQO ⁇ (
  • Aphids are killed to 90% and caterpillars are completely destroyed by 0.01% solutions of the compound. Spider mites are killed to 40% by 0.001% solutions of the ester. Moreover the product shows an ovicidal activity against the eggs of the last mentioned pests.
  • hexyl-S-(B-et-hylmercaptoethyl)-thiolphosphoric acid ester are thus formed of B.P. 112 C./0.01 mm. Hg.
  • Example 7 114 g. (0.5 mol) of O-methyl-O-cyclohexyl-thiophos phoric acid ammonium salt are dissolved in 250 cc. of acetonitrile. 67 g. of fl-chloropropionitrile are added to the solution at 80 C. with stirring. Subsequently the mixture is stirred at 80 C. for a further 2 hours and then worked up as described in Example 1b. 56 g. of O-methyl-O-cyclohexyl-S-(fi-cyanethyl) thiolphosphoric acid ester of B.P. 108 C./ 0.01 mm. Hg are thus obtained.
  • Example 8 114 g. (0.5 mol) of O-methyl-O-cyclohexyl-thiophosphoric acid ammonium salt are dissolved in 250 cc. of acctonitrile. 56 g. of chloromethyl-thioethyl ether are added to this solution at 50 to 60 C. With stirring. The temperature of the reaction mixture is maintained at 60 C. for 1 hour and the mixture is then worked up as described in Example 115. 74 g.
  • Spider mites are completely destroyed by 0.01% solutions of the compound and caterpillars are killed to 40% even by 0.001% solutions. Moreover the ester shows an ovicidal activity against the eggs of spider mites.
  • Example 9 94 g. (0.5 mol) of O-methyl-O-isopropylthiophosphoric acid ammonium salt are slurried in 250 cc. of acetonitrile and 36 g. (0.5 mol) of chloroacetonitrile are added with stirring at 50 to 60 C. to this slurry. Subsequently the reaction mixture is stirred for 3 hours at 60 C. and then poured into 300 cc. of ice-water and the separated oil is absorbed in 300 cc. of benzene. The benzene solution is washed with water and then dried over sodium sulphate. After distilling off the solvent there are obtained 75 g.
  • Example sHrO O 94 g. (0.5 mol) of O-methyl-O-isopropyl-thiophosphoric acid ammonium salt are slurried in 250 cc. of acetonitrile. To this slurry there are added 67 g. (0.5 mol) of B-chloropropionitrile with strong stirring at 75 C. Subsequently the reaction mixture is stirred for 3 hours at 75 to 80% C. and then poured into 300 cc. of ice-Water. The separated oil is absorbed in 300 cc. of benzene. The benzene solution is Washed with water and dried over sodium sulphate. After distilling off the solvent there are obtained 62 g.
  • Example 11 CH O To a solution of 94 g. (0.5 mol) of O-methyl-O-isopropyl-thiophosphoric acid ammonium salt in 300 cc. of acetonitrile there are added at 70 C. 54 g. (0.5 mol) of chloro acetic .acid-N-methyl-amide, dissolved in 50 cc. of acetonitrile, the reaction mixture is stirred for 2 hours at the stated temperature and then poured into 400 cc. of ice-water. The separated oil is absorbed in 300 cc. of chloroform and the solution in chloroform dried over sodium sulphate. Subsequently the solvent is removed by distillation. A residue of 71 g. (59% of the theoretical yield) of O-methyl-O-isopropyl-S-(N-methyl-carbaminyl-methyl-)-thiolphospboric acid ester as a viscous, water-insoluble oil is obtained.
  • the mean toxicity of the compound (LD on rats per os amounts to 10 mg. per kg. of animal.
  • Example 12 In an analogous manner as described inthe aforementioned Examples there is obtained from 114 g. (0.5 mol) of O-methyl-O-cyclohexylthiophosphoric acid ammonium salt by the reaction with 54 g. of chloro acetic acid-N- methylamide the -O-methyl-O-cyclohexyl-S-(N-methylcarbaminyl-methyl-)-thiolphosphoric acid ester as a lightyellow, viscous, Water-soluble oil.
  • the mean toxicity of the compound (LD on rats per os amount to 50 mg. per kg. of animal.
  • the yield amounts to 64 g. (78% of the theoretical).
  • the mean toxicity of the compound (LD on rats per os amounts to 5 mg. per kg. of animal.
  • Spider mites are killed to 80% by 0.00016% solutions of the ester.
  • the systemic action of 0.00016% solutions against aphids is Example 14 iC H7O ⁇ (
  • O-methyl-O-isopropylthiophosphoric acid ammonium salt and 56 g. (0.5 mol) of chloro-methylthioethylether 67 g. (55% of the theoretical yield) of O-methyl O isopropyl-S-(-ethylmercapto-methyl)-thiolphosphoric acid ester as a Water insoluble colourless oil of B.P. 74 C./0.01 mm. Hg and the refractive index 12 1.4968.
  • Caterpillars are completely destroyed by 0.01% solutions and spider mites are killed to 80% even 'by 0.0001% solutions of the ester.
  • Example 15 SCH5 10,1170 0 I 38 g. (0.5 mol) of ,8-chloroethylthioethylether are 94 g. (0.5 mol) of O-methyl-O-isopropyl-thiophosphoric acid ammonium salt are dissolved in 300 cc. of acetonitrile. 95 g. of 2-methylrnercapto-S-methyl-benzyl-chloride are added with stirring to this solution at 75 C. Subsequently the reaction mixture is stirred for 2 hours at 80 C. and Worked up as mentioned in the aforesaid example. In this way there are obtained 122 g. (76% of the theoretical yield) of O-methyl-O-isopropyl-S-(2- rnethylmercapto 5 methyl-benzyl)thiolphosphoric acid ester as a colourless, water insoluble oil.
  • Spider mites are completely destroyed by 0.01% solutions of the ester; moreover the compound shows an ovicidal activity against the eggs of the mentioned pests.
  • Example 16 CHaO On rats per os the compound possesses a mean toxicity (LD of 250 mg. per kg. of animal.
  • Spider mites are completely destroyed by 0.01% solutions of the ester. Moreover the compound shows an ovicidal activity against the eggs of these pests.
  • ) PSR2 wherein R stands for cyclohexyl, R stands for lower alkyl having up to 4 carbon atoms and R stands for a member selected from the group consisting of lower alkyl mercapto substituted lower alkyl, phenyl substituted lower alkyl, chlorophenyl substituted lower alkyl, lower alkyl mercapto phenyl substituted lower alkyl, lower alkyl and lower alkyl mercapto-phenyl substituted lower alkyl, phen- 5 ylmercapto substituted lower alkyl and chloro phenyl mercapto substituted lower alkyl, lower alkyl in each case having up to 4 carbon atoms.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US253070A 1962-01-24 1963-01-22 Omicron-alkyl-omicron-cycloalkyl-s-alkylthiolphosphoric acid esters Expired - Lifetime US3294874A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF35839A DE1172667B (de) 1962-01-24 1962-01-24 Verfahren zur Herstellung von O, O-Dialkyl-S-alkylthiolphosphorsaeureestern

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US (1) US3294874A (fr)
BR (1) BR6346394D0 (fr)
CH (1) CH426776A (fr)
DE (1) DE1172667B (fr)
DK (1) DK109851C (fr)
GB (1) GB977819A (fr)
NL (2) NL136286C (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3725514A (en) * 1968-11-12 1973-04-03 Sumitomo Chemical Co O-aryl o-alkyl s-organo phosphorothidates
US3897552A (en) * 1971-08-18 1975-07-29 Bayer Ag Fungicidal and bactericidal O-alkyl-O-cyclohexyl-S-alkyl-, haloalkyl-or alkenyl-phosphorothiolates
US3927148A (en) * 1971-08-19 1975-12-16 Exxon Research Engineering Co O,S{40 -Dialkyl-S-hydrocarbylthioalkyl dithiophosphates
JPS51136654A (en) * 1976-04-27 1976-11-26 Nippon Tokushu Noyaku Seizo Kk Process for preparation of o-cyclohexyl-o-alkyl-s-(halo or alkenyl)pho sphorothiolate
US4755311A (en) * 1986-08-14 1988-07-05 The Lubrizol Corporation Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same
WO1992004358A1 (fr) * 1990-09-04 1992-03-19 Gen-Probe Incorporated Methode et reactif pour la sulfuration de composes organophosphoreux
US5252723A (en) * 1989-03-06 1993-10-12 Gen-Probe, Inc. Method and reagent for sulfurization of organophosphorous compounds
EP0723968A2 (fr) * 1995-01-25 1996-07-31 Bayer Ag Procédé de préparation de 0,0'-diesters d'acide thiophosphorique et leurs sels ainsi que leur utilisation

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2494284A (en) * 1949-01-12 1950-01-10 American Cyanamid Co Cyanoalkyl phosphates and method of preparation
US2494283A (en) * 1948-02-04 1950-01-10 American Cyanamid Co Carbamylalkyl phosphates and method of preparation
US2597534A (en) * 1949-05-07 1952-05-20 Bayer Ag Neutral esters of thiolphosphoric acid
US2938919A (en) * 1958-02-06 1960-05-31 Bayer Ag Thiophosphoric acid esters and a process for their manufacture
US3020305A (en) * 1958-08-25 1962-02-06 Monsanto Chemicals Halogen substituted alkenylthioalkyl esters of phosphorus acids

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE539662A (fr) * 1954-09-29
DE949231C (de) * 1955-05-03 1956-09-13 Bayer Ag Verfahren zur Herstellung von chlkorierten Benzylestern der Thiol- bzw. Thionothiolphosphorsaeuren
DE1024509B (de) * 1956-03-03 1958-02-20 Bayer Ag Verfahren zur Herstellung von O, O-Dialkyl-thiol-phosphorsaeure- und -thiol-thiono-phsphorsaeureestern
DE1116657B (de) * 1960-01-22 1961-11-09 Bayer Ag Verfahren zur Herstellung von Derivaten der Thiosaeuren des Phosphors

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2494283A (en) * 1948-02-04 1950-01-10 American Cyanamid Co Carbamylalkyl phosphates and method of preparation
US2494284A (en) * 1949-01-12 1950-01-10 American Cyanamid Co Cyanoalkyl phosphates and method of preparation
US2597534A (en) * 1949-05-07 1952-05-20 Bayer Ag Neutral esters of thiolphosphoric acid
US2938919A (en) * 1958-02-06 1960-05-31 Bayer Ag Thiophosphoric acid esters and a process for their manufacture
US3020305A (en) * 1958-08-25 1962-02-06 Monsanto Chemicals Halogen substituted alkenylthioalkyl esters of phosphorus acids

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3725514A (en) * 1968-11-12 1973-04-03 Sumitomo Chemical Co O-aryl o-alkyl s-organo phosphorothidates
US3897552A (en) * 1971-08-18 1975-07-29 Bayer Ag Fungicidal and bactericidal O-alkyl-O-cyclohexyl-S-alkyl-, haloalkyl-or alkenyl-phosphorothiolates
US3927148A (en) * 1971-08-19 1975-12-16 Exxon Research Engineering Co O,S{40 -Dialkyl-S-hydrocarbylthioalkyl dithiophosphates
JPS51136654A (en) * 1976-04-27 1976-11-26 Nippon Tokushu Noyaku Seizo Kk Process for preparation of o-cyclohexyl-o-alkyl-s-(halo or alkenyl)pho sphorothiolate
US4755311A (en) * 1986-08-14 1988-07-05 The Lubrizol Corporation Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same
US5252723A (en) * 1989-03-06 1993-10-12 Gen-Probe, Inc. Method and reagent for sulfurization of organophosphorous compounds
US5449769A (en) * 1989-03-06 1995-09-12 Gen-Probe Incorporated Method and reagent for sulfurization of organophosphorous compounds
WO1992004358A1 (fr) * 1990-09-04 1992-03-19 Gen-Probe Incorporated Methode et reactif pour la sulfuration de composes organophosphoreux
EP0723968A2 (fr) * 1995-01-25 1996-07-31 Bayer Ag Procédé de préparation de 0,0'-diesters d'acide thiophosphorique et leurs sels ainsi que leur utilisation
EP0723968A3 (fr) * 1995-01-25 1997-10-29 Bayer Ag Procédé de préparation de 0,0'-diesters d'acide thiophosphorique et leurs sels ainsi que leur utilisation

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Publication number Publication date
GB977819A (en) 1964-12-16
BR6346394D0 (pt) 1973-08-09
DK109851C (da) 1968-07-15
NL288076A (fr)
CH426776A (de) 1966-12-31
NL136286C (fr)
DE1172667B (de) 1964-06-25

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