GB956244A - Triazinyl alkyl thiophosphate esters, method of preparation, and pesticidal compositions containing same - Google Patents

Triazinyl alkyl thiophosphate esters, method of preparation, and pesticidal compositions containing same

Info

Publication number
GB956244A
GB956244A GB9796/61A GB979661A GB956244A GB 956244 A GB956244 A GB 956244A GB 9796/61 A GB9796/61 A GB 9796/61A GB 979661 A GB979661 A GB 979661A GB 956244 A GB956244 A GB 956244A
Authority
GB
United Kingdom
Prior art keywords
alkyl
defined above
alkyl radical
radical
hydrogen
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
Application number
GB9796/61A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB956244A publication Critical patent/GB956244A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00—Halogens; Halogen acids
    • C01B7/09—Bromine; Hydrogen bromide
    • C01B7/096—Bromine
    • 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
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
    • C07F9/6521—Six-membered rings

Abstract

The invention comprises triazinyl alkyl thiophosphate esters of the general formula: <FORM:0956244/C2/1> wherein R and R1 are C1-C6 alkyl radicals, R2, R3 and B each represent hydrogen or a C1-C6 alkyl radical, Y and Y1 represent oxygen or sulphur at least one of Y and Y1 being oxygen and D is hydrogen, a C1-C6 alkyl radical or the radical: <FORM:0956244/C2/2> wherein R, R1, R2, R3, Y and Y1 are as defined above. They may be obtained by reacting a salt of a dialkyl thiophosphoric acid of the formula: <FORM:0956244/C2/3> wherein R, R1, Y and Y1 are as defined above and M is ammonium or an alkali metal, e.g. Na, K, or Li, with a haloalkyl substituted s-triazine of the formula: <FORM:0956244/C2/4> wherein R2, R3 and B are as defined above, X is halogen and Z is H, a C1-C6 alkyl radical or: <FORM:0956244/C2/5> When Z has the latter meaning at least two moles of the salt is reacted with 1 mole of the haloalkyl substituted s-triazine to form the product in which D is: <FORM:0956244/C2/6> The reaction is generally carried out in an inert organic solvent, e.g. acetone, methyl isobutyl ketone, alcohol, ether, benzene or a chlorinated hydrocarbon. The reaction may also be carried out by using the free dialkyl thiophosphoric acid in the presence of an appropriate hydrogen halide acceptor, e.g. an alkali metal carbonate or bicarbonate or an alkaline earth metal carbonate. Preferred reaction temperatures are from 10 DEG C. to 150 DEG C. The products have pesticidal properties (see Division A5). The haloalkyl-substituted s-triazines used as starting materials may be obtained by reacting a haloamidine having the guanyl grouping <FORM:0956244/C2/7> with an imidate, thus 1 mol of 1-chloroacetamidine hydrochloride or of 1-chloro-propionamidine hydrochloride and 3 mols of ethyl acetimidate may be reacted to form a mixture of monochloroalkyl -striazine and bis (chloroalkyl) -striazine which may then be recovered separately.ALSO:A pesticidal composition comprises an inert carrier and a triazinyl alkyl thiophosphate ester having the formula <FORM:0956244/A5-A6/1> wherein R and R1 are C1-C6 alkyl radicals, R2, R3 and B each represent hydrogen or a C1-C6 alkyl radical, Y and Y1 represent oxygen or sulphur at least one of Y and Y1 being oxygen, and D is hydrogen, a C1-C6 alkyl radical or the radical <FORM:0956244/A5-A6/2> wherein R, R1, R2, R3, Y and Y1 are as defined above (see Division C2). The composition may be in the form of a dust formed by using a finely-divided inert carrier or in the form of a liquid concentrate prepared by using an organic solvent such as acetone or xylene and an emulsifying agent. The composition may also be in a form suitable for use as an aerosol by using a compressed halogenated hydrocarbon gas such as dichloro-difluoro methane.
GB9796/61A 1960-05-31 1961-03-17 Triazinyl alkyl thiophosphate esters, method of preparation, and pesticidal compositions containing same Expired GB956244A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US3260360A 1960-05-31 1960-05-31

Publications (1)

Publication Number Publication Date
GB956244A true GB956244A (en) 1964-04-22

Family

ID=21865804

Family Applications (2)

Application Number Title Priority Date Filing Date
GB9796/61A Expired GB956244A (en) 1960-05-31 1961-03-17 Triazinyl alkyl thiophosphate esters, method of preparation, and pesticidal compositions containing same
GB18959/61A Expired GB930341A (en) 1960-05-31 1961-05-25 Catalytic oxidation of hydrobromic acid with air

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB18959/61A Expired GB930341A (en) 1960-05-31 1961-05-25 Catalytic oxidation of hydrobromic acid with air

Country Status (5)

Country Link
BE (1) BE601889A (en)
DE (1) DE1292639B (en)
FR (1) FR1288314A (en)
GB (2) GB956244A (en)
NL (1) NL262753A (en)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3179498A (en) * 1963-12-02 1965-04-20 Air Prod & Chem Recovery of bromine by the nitrite catalytic oxidation of bromide ion in an acid medium
US3353916A (en) * 1966-04-25 1967-11-21 Universal Oil Prod Co Quantitative recovery of bromine by two stage catalytic oxidation of hydrogen bromide
US3437445A (en) * 1967-04-19 1969-04-08 Gulf Research Development Co Process for oxidizing hydrogen bromide to obtain bromine
EP0626885A4 (en) * 1992-02-04 1995-11-22 Catalytica Inc Cebr 3? catalyst and process for producing bromine.
US20080275284A1 (en) 2004-04-16 2008-11-06 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US7244867B2 (en) 2004-04-16 2007-07-17 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
DE602007008255D1 (en) * 2006-08-25 2010-09-16 Albemarle Corp METHOD OF OXIDIZING BROMIDES FOR THE PREPARATION OF BROMINES AND CATALYSTS THEREOF
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
EP2399888A1 (en) * 2008-07-18 2011-12-28 GRT, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
US8829256B2 (en) 2011-06-30 2014-09-09 Gtc Technology Us, Llc Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
US20130156681A1 (en) * 2011-12-19 2013-06-20 Marathon Gtf Technology, Ltd. Processes and Systems for Oxidizing Aqueous Metal Bromide Salts

Also Published As

Publication number Publication date
NL262753A (en) 1964-05-25
BE601889A (en) 1961-09-28
FR1288314A (en) 1962-03-24
GB930341A (en) 1963-07-03
DE1292639B (en) 1969-04-17

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