GB993051A - N-substituted methylamides and pesticidal compositions containing them - Google Patents

N-substituted methylamides and pesticidal compositions containing them

Info

Publication number
GB993051A
GB993051A GB1812660A GB1812660A GB993051A GB 993051 A GB993051 A GB 993051A GB 1812660 A GB1812660 A GB 1812660A GB 1812660 A GB1812660 A GB 1812660A GB 993051 A GB993051 A GB 993051A
Authority
GB
United Kingdom
Prior art keywords
alkyl
socl2
formamide
hydrogen
nhcoy
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
GB1812660A
Inventor
Max Pianka
John Duncan Edwards
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.)
Murphy Chemical Co Ltd
Original Assignee
Murphy Chemical Co Ltd
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 Murphy Chemical Co Ltd filed Critical Murphy Chemical Co Ltd
Publication of GB993051A publication Critical patent/GB993051A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/58—One oxygen atom, e.g. butenolide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises the compounds of formula Z-CHX.NHCOY or D(CHZ.NHCOY)2, where Z is hydrogen or trihalogenomethyl, X is (i) RR1NCSS-, (ii) R1OCSS- (where R is hydrogen or C1- 3 alkyl and R1 is C1- 3 alkyl) or (iii) the group <FORM:0993051/C2/1> Y is hydrogen, alkyl, alkenyl, halogenoalkyl, phenyl, halogenophenyl, nitrophenyl, RR1NCSS-alkyl, R1OCSS-alkyl, alkoxy, halogenoalkoxy, furyl or alkoxyphenyl, and D is an alkylene bis-dithiocarbanoyl group; and their production by reacting a compound ZCHHal.NHCOY where Hal is chlorine, bromine or iodine, with MX or M2D, where M is alkali metal or ammonium, e.g. in acetone or aqueous acetone, preferably at from -60 DEG to +40 DEG C. The compounds of the invention are pesticides (see Division A5). Intermediates in Examples.-(1) Methyl carbamate and chloral give N-(1-hydroxy-2,2,2-trichloroethyl) methyl carbamate, which with SOCl2 gives N-(1,2,2,2-tetrachloroethyl) methyl carbamate; (2), (3) the corresponding carbamate ethyl and butyl esters are prepared similarly; (II) formamide and chloral react to give N-(1-hydroxy-2,2,2-trichloroethyl) formamide, which with SOCl2 produces N-(1,2,2,2-tetrachloroethyl) formamide; (23) formamide and bromal were similarly reacted to give N-(1 - hydroxy - 2,2,2 - tribromoethyl) formamide, which with SOCl2 produces N-(1-chloro-2,2,2-tribromoethyl) formamide; (25) N-methylol-acetamide is obtained from acetamide and formaldehyde, and is reacted with SOCl2 to give chloromethyl acetamide; (26) and (32) N-methylol chloroacetamide and SOCl2 provide N-chloromethyl chloroacetamide; and (27) N-methylol fluoroacetamide is prepared from fluoroacetamide and formaldehyde, and with SOCl2 gives N-chloromethyl fluoroacetamide. Specification 993,053 is referred to.ALSO:The invention comprises pesticidal compositions containing a compound XCHZ.NHCOY or D(CHZ.NHCOY)2, where Z is hydrogen or trihalogenomethyl; X is (i) RR1NCSS-, (ii) R1OCSS- (where R is hydrogen or C1-3 alkyl and R1 is C1-3 alkyl) or (iii) the group <FORM:0993051/A5-A6/1> Y is hydrogen, alkyl, alkenyl, halogenoalkyl, phenyl, halogenophenyl, nitrophenyl, RR1NCSS- alkyl, R1OCSS- alkyl, alkoxy, halogenoalkoxy, furyl or alkoxyphenyl, and D is an alkylene bis-dithiocarbamoyl group (see Division C2) in association with a carrier or diluent. China clay is used as diluent in some examples. The compositions may be solutions, emulsions, aerosols, dusts, wettable powders, granulates, pellets, pastes or thermal fumigating mixtures. Specification 993,053 is referred to.
GB1812660A 1965-04-26 1960-05-23 N-substituted methylamides and pesticidal compositions containing them Expired GB993051A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL6505317A NL6505317A (en) 1965-04-26 1965-04-26

Publications (1)

Publication Number Publication Date
GB993051A true GB993051A (en) 1965-05-26

Family

ID=19793032

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1812660A Expired GB993051A (en) 1965-04-26 1960-05-23 N-substituted methylamides and pesticidal compositions containing them

Country Status (3)

Country Link
CH (1) CH453789A (en)
GB (1) GB993051A (en)
NL (1) NL6505317A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3504029A (en) * 1966-02-02 1970-03-31 Bayer Ag Fluoroacylamino-trichloromethyl-methane derivatives
FR2450253A1 (en) * 1979-02-27 1980-09-26 Nippon Kayaku Kk 2-HYDROXYBENZAMIDE DERIVATIVES, COMPOSITION AND METHOD USING SUCH DERIVATIVES AS FUNGICIDES

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3504029A (en) * 1966-02-02 1970-03-31 Bayer Ag Fluoroacylamino-trichloromethyl-methane derivatives
FR2450253A1 (en) * 1979-02-27 1980-09-26 Nippon Kayaku Kk 2-HYDROXYBENZAMIDE DERIVATIVES, COMPOSITION AND METHOD USING SUCH DERIVATIVES AS FUNGICIDES

Also Published As

Publication number Publication date
CH453789A (en) 1968-03-31
NL6505317A (en) 1966-10-27

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