GB1419987A - Carbamoylvinyl phosphate and carbamoylvinyl phosphonate insecticides - Google Patents

Carbamoylvinyl phosphate and carbamoylvinyl phosphonate insecticides

Info

Publication number
GB1419987A
GB1419987A GB456573A GB456573A GB1419987A GB 1419987 A GB1419987 A GB 1419987A GB 456573 A GB456573 A GB 456573A GB 456573 A GB456573 A GB 456573A GB 1419987 A GB1419987 A GB 1419987A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
prepared
reacting
compound
formula
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
GB456573A
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.)
ExxonMobil Oil Corp
Original Assignee
Mobil Oil Corp
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 Mobil Oil Corp filed Critical Mobil Oil Corp
Publication of GB1419987A publication Critical patent/GB1419987A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/40—Esters thereof
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4078—Esters with unsaturated acyclic alcohols

Abstract

1419987 Insecticidal cabamoylvinyl phosphates and phosphonates MOBIL OIL CORP 30 Jan 1973 [29 Feb 1972 10 Jan 1973] 4565/73 Headings C2P and C2C The invention comprises compounds of Formula I where X, Y and W are O or S, R 1 , R 2 , R 3 snd R 4 are H or optionally substituted C 1-8 alkyl, C 3-8 cycloalkyl, C 2-8 alkenyl, C 1-8 alkoxy, aryl, C 7-14 aralkyl, acetyl, carbalkoxy, C 1-8 alkylthio or mono- or dialkyl-carbamoyl or R 1 and R 2 together with N form a 5- or 6-membered ring and Q and Z are as defined for R 1 , R 2 , R 3 and R 4 or are Cl, Br, F, CN or alkylsulphonyl. The compounds of Formula I may be prepared by reacting a beta-chlorinated alphaoxocarboxylic acid amide with an appropriate trivalent phosphorus ester or by reacting an appropriately-substituted pyruvamide with an appropriate trivalent phosphorus compound in the presence of a base formed in situ from the phosphorus compound and bromotrichloromethane used as solvent. Starting materials are prepared as follows: N,N-dimethyl- and N,N-diethyl-3,3,3-trichloropyruvamide; N,N-dimethyl-3,3,3-trichloro-1-thiopyruvamide; and N,N-dimethyl-3,3-dichloro-2- oxobutyramide are prepared by reacting trichloroacetyl chloride with dimethyl formamide, diethyl formamide or N,N-dimethylthioformamide or reacting 2,2-dichloropropionyl chloride with dimethyl formamide respectively; N,N- dimethyl-3,3-dichloropyruvamide and N,N-dimethyl-3-chloropyruvamide are prepared by hydrogenating the corresponding 3,3,3-trichloro compound; N,N-dimethyl-3-chloro-2-oxobutyramide is prepared by hydrogenating the corresponding 3,3-dichloro compound; and N,N- dimethyl 3-methylthiopyruvamide is prepared by reacting the corresponding 3-chloro compound with methyl mercaptan. The compounds of Formula I have insecticidal properties and may be used as active ingredients in conventional pesticidal compositions.
GB456573A 1972-02-29 1973-01-30 Carbamoylvinyl phosphate and carbamoylvinyl phosphonate insecticides Expired GB1419987A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US23047572A 1972-02-29 1972-02-29

Publications (1)

Publication Number Publication Date
GB1419987A true GB1419987A (en) 1976-01-07

Family

ID=22865374

Family Applications (1)

Application Number Title Priority Date Filing Date
GB456573A Expired GB1419987A (en) 1972-02-29 1973-01-30 Carbamoylvinyl phosphate and carbamoylvinyl phosphonate insecticides

Country Status (2)

Country Link
DE (1) DE2310037A1 (en)
GB (1) GB1419987A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1392639A1 (en) * 2001-05-03 2004-03-03 Galileo Laboratories, Inc. Pyruvate derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1392639A1 (en) * 2001-05-03 2004-03-03 Galileo Laboratories, Inc. Pyruvate derivatives
EP1392639A4 (en) * 2001-05-03 2006-01-25 Galileo Lab Inc Pyruvate derivatives

Also Published As

Publication number Publication date
DE2310037A1 (en) 1973-09-13

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees