GB1269400A - alpha-IMIDOACRYLATES HAVING INSECTICIDAL ACTIVITY - Google Patents

alpha-IMIDOACRYLATES HAVING INSECTICIDAL ACTIVITY

Info

Publication number
GB1269400A
GB1269400A GB5750669A GB5750669A GB1269400A GB 1269400 A GB1269400 A GB 1269400A GB 5750669 A GB5750669 A GB 5750669A GB 5750669 A GB5750669 A GB 5750669A GB 1269400 A GB1269400 A GB 1269400A
Authority
GB
United Kingdom
Prior art keywords
methyl
formula
hydrogen
ester
dimethylacrylate
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
GB5750669A
Inventor
Allan Guildford Brown
Terence Charles Smale
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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
Priority to BE758473D priority Critical patent/BE758473A/en
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Priority to GB5750669A priority patent/GB1269400A/en
Priority to NL7016248A priority patent/NL7016248A/xx
Priority to FR7040642A priority patent/FR2068629B1/fr
Priority to DE19702058012 priority patent/DE2058012A1/en
Publication of GB1269400A publication Critical patent/GB1269400A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom

Abstract

1,269,400. α-Imidoacrylic esters. BEECHAM GROUP Ltd. 29 Oct., 1970 [25 Nov., 1969], No. 57606/69. Heading C2C. Novel α-imido acrylates of the formula in which R<SP>1</SP> and R<SP>2</SP> are each hydrogen or methyl groups, R<SP>3</SP> is C 1-6 alkyl, R<SP>4</SP> and R<SP>5</SP> are each hydrogen or C 1-6 alkyl and R<SP>6</SP> and R<SP>7</SP> are each hydrogen or methyl groups or together represent a double bond in the imide ring, provided that R<SP>3</SP> is not methyl when R<SP>1</SP>, R<SP>2</SP>, R<SP>4</SP>, R<SP>6</SP> and R<SP>7</SP> are hydrogen and R<SP>5</SP> is methyl, are prepared by heating an anhydride of the formula with either an unsaturated amino ester of the formula or a hydroxy amino ester of the formula The known compound, methyl 2-(methylsuccinimido)-acrylate, is made by an analogous method. The reaction with the hydroxyamino ester III may proceed in 2 steps, an intermediate α-imido-#-hydroxy ester of the formula being isolated, such intermediates in which R<SP>6</SP> and R<SP>7</SP> represent a double bond being optionally hydrogenated to the corresponding saturated compounds. Examples describe the preparation of a variety of imides. Methyl 2-amino-3,3-dimethylacrylate is prepared by aluminum amalgam reduction of methyl 2-nitro-3,3-dimethylacrylate which is obtained by nitration of methyl 3,3-dimethylacrylate. Serine methyl ester hydrochloride is obtained by reaction of serine with methanolic HCl. The novel α-imidoacrylates are used in conventional forms as insecticides.
GB5750669A 1969-11-25 1969-11-25 alpha-IMIDOACRYLATES HAVING INSECTICIDAL ACTIVITY Expired GB1269400A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE758473D BE758473A (en) 1969-11-25 ALPHA-IMIDO ACRYLIC ESTERS INSECTICIDES
GB5750669A GB1269400A (en) 1969-11-25 1969-11-25 alpha-IMIDOACRYLATES HAVING INSECTICIDAL ACTIVITY
NL7016248A NL7016248A (en) 1969-11-25 1970-11-05
FR7040642A FR2068629B1 (en) 1969-11-25 1970-11-13
DE19702058012 DE2058012A1 (en) 1969-11-25 1970-11-25 Alpha-imidoacrylic acid esters, process for their preparation and their use as insecticides or in insecticides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5750669A GB1269400A (en) 1969-11-25 1969-11-25 alpha-IMIDOACRYLATES HAVING INSECTICIDAL ACTIVITY

Publications (1)

Publication Number Publication Date
GB1269400A true GB1269400A (en) 1972-04-06

Family

ID=10479353

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5750669A Expired GB1269400A (en) 1969-11-25 1969-11-25 alpha-IMIDOACRYLATES HAVING INSECTICIDAL ACTIVITY

Country Status (5)

Country Link
BE (1) BE758473A (en)
DE (1) DE2058012A1 (en)
FR (1) FR2068629B1 (en)
GB (1) GB1269400A (en)
NL (1) NL7016248A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4539208A (en) * 1980-09-17 1985-09-03 Merck & Co., Inc. Combination of thienamycin-type antibiotics with dipeptidase inhibitors
US4880793A (en) * 1978-07-24 1989-11-14 Merck & Co., Inc. Combination of thienamycin-type antibiotics with dipeptidase inhibitors

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4880793A (en) * 1978-07-24 1989-11-14 Merck & Co., Inc. Combination of thienamycin-type antibiotics with dipeptidase inhibitors
US4539208A (en) * 1980-09-17 1985-09-03 Merck & Co., Inc. Combination of thienamycin-type antibiotics with dipeptidase inhibitors

Also Published As

Publication number Publication date
FR2068629A1 (en) 1971-08-27
NL7016248A (en) 1971-05-27
BE758473A (en) 1971-05-04
FR2068629B1 (en) 1973-02-02
DE2058012A1 (en) 1971-06-03

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