GB1522869A - Substituted 4- halomethyl 2- pyrrolidinones and the use thereof as herbicides - Google Patents

Substituted 4- halomethyl 2- pyrrolidinones and the use thereof as herbicides

Info

Publication number
GB1522869A
GB1522869A GB11627/76A GB1162776A GB1522869A GB 1522869 A GB1522869 A GB 1522869A GB 11627/76 A GB11627/76 A GB 11627/76A GB 1162776 A GB1162776 A GB 1162776A GB 1522869 A GB1522869 A GB 1522869A
Authority
GB
United Kingdom
Prior art keywords
pyrrolidinones
halomethyl
herbicides
substituted
alkenylhalocyanamides
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
GB11627/76A
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.)
Stauffer Chemical Co
Original Assignee
Stauffer Chemical 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
Priority claimed from US05/647,962 external-priority patent/US4069038A/en
Priority claimed from US05/647,963 external-priority patent/US4110105A/en
Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co
Publication of GB1522869A publication Critical patent/GB1522869A/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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The herbicidal preparation contains, as active component, a compound of the formula I. The substituents have the meaning given in the patent claim. The abovementioned compounds are prepared by cyclization of corresponding N-alkenylhalocyanamides in the presence of a catalytic amount of iron(II) ions. <IMAGE>
GB11627/76A 1975-03-28 1976-03-23 Substituted 4- halomethyl 2- pyrrolidinones and the use thereof as herbicides Expired GB1522869A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US56327975A 1975-03-28 1975-03-28
US56328075A 1975-03-28 1975-03-28
US05/647,962 US4069038A (en) 1975-03-28 1976-01-09 Acyclic and alicyclic N-substituted halo-2-pyrrolidinones and their utility as herbicides
US05/647,963 US4110105A (en) 1975-03-28 1976-01-09 Aromatic N-substituted halo-substituted-2-pyrrolidinones and their utility as herbicides

Publications (1)

Publication Number Publication Date
GB1522869A true GB1522869A (en) 1978-08-31

Family

ID=27504836

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11627/76A Expired GB1522869A (en) 1975-03-28 1976-03-23 Substituted 4- halomethyl 2- pyrrolidinones and the use thereof as herbicides

Country Status (25)

Country Link
JP (1) JPS6011695B2 (en)
AU (1) AU502662B2 (en)
BE (1) BE839977A (en)
BG (2) BG29122A3 (en)
BR (1) BR7601774A (en)
CA (1) CA1076588A (en)
CH (1) CH625394A5 (en)
DD (1) DD126149A5 (en)
DE (2) DE2661042C2 (en)
DK (1) DK145891C (en)
ES (1) ES446388A1 (en)
FR (1) FR2305434A1 (en)
GB (1) GB1522869A (en)
HU (1) HU179058B (en)
IL (1) IL49289A (en)
IN (1) IN143281B (en)
IT (1) IT1057396B (en)
MX (1) MX3355E (en)
MY (1) MY8000091A (en)
NL (1) NL187313C (en)
NZ (1) NZ180424A (en)
PH (1) PH15176A (en)
PL (2) PL102693B1 (en)
SU (1) SU942590A3 (en)
YU (1) YU40279B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4701560A (en) * 1985-05-22 1987-10-20 Rhone-Poulenc Specialties Chimiques Process for the preparation of N-2-alkenyl-m-trifluoromethylanilines
US5538985A (en) * 1994-01-27 1996-07-23 Mitsui Toatsu Chemicals, Inc. Pyrrolidinone derivatives
CN114031536A (en) * 2021-12-14 2022-02-11 青海省农林科学院 Pure optical isomer compound for inhibiting weed seed germination and seedling growth and application

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU527254B2 (en) * 1979-02-26 1983-02-24 Stauffer Chemical Company Synergistic herbicides
EP0055215B1 (en) * 1980-12-19 1985-01-30 Ciba-Geigy Ag Fluoropyrrolidinones, process for their preparation, herbicides containing them and their use
DK162087C (en) * 1983-06-16 1992-02-24 Stauffer Chemical Co PROCEDURE FOR THE PREPARATION OF N-ARYLHALOGEN PYROLIDONES
FI74385C (en) * 1983-12-05 1988-02-08 Stauffer Chemical Co SYNERGISTIC HERBICIDBLANDNINGAR AV TIOKARBAMAT OCH PYRROLIDONFOERENING.
FR2589150B2 (en) * 1985-10-25 1987-11-20 Rhone Poulenc Spec Chim PROCESS FOR THE PREPARATION OF N ALCENE-2 YL M.TRIFLUOROMETHYLANILINES
FR2582300B1 (en) * 1985-05-22 1987-07-10 Rhone Poulenc Spec Chim PROCESS FOR THE PREPARATION OF N-2 ALCENE-2 YL M-TRIFLUOROMETHYLANILINES
FR2625197B1 (en) * 1987-12-23 1990-04-27 Rhone Poulenc Chimie PROCESS FOR ACYLATION OF N, N-DIALLYLANILINE
US5189220A (en) * 1988-07-29 1993-02-23 Rhone-Poulenc Chimie Process for preparing N-alkylanilines and N-allylanilines catalyzed by iodides
FR2634761B1 (en) * 1988-07-29 1990-11-23 Rhone Poulenc Chimie PROCESS FOR THE PREPARATION OF N-ALLYL AND N-ALKYLANILINES
US5210305A (en) * 1988-07-29 1993-05-11 Rhone-Poulenc Chimie Process for preparing n-alkylanilines and n-allylanilines
FR2634762B1 (en) * 1988-07-29 1990-11-02 Rhone Poulenc Chimie PROCESS FOR THE PREPARATION OF N-ALLYL AND ALKYL-ANILINES
FR2643902B1 (en) * 1989-03-03 1991-10-11 Rhone Poulenc Chimie PROCESS FOR THE PREPARATION OF N-ALLYLMETATRIFLUOROMETHYLANILINE
JPH02237970A (en) * 1989-03-13 1990-09-20 Mitsui Toatsu Chem Inc 4-ethyl-1-(3-trifluoromethylphenyl)-2-pyrrolidinone derivative and herbicide containing the derivative as active component
FR2663927A1 (en) * 1989-06-05 1992-01-03 Rhone Poulenc Chimie PROCESS FOR THE PREPARATION OF N MONOALKYL- OR ALKENYLANILINES.
JP2728937B2 (en) * 1989-06-14 1998-03-18 三井東圧化学株式会社 1- (3-Substituted benzyl) -3-halogen-4- (1-halogenoalkyl) -2-pyrrolidinone derivatives and herbicides containing these as active ingredients
FR2665439B1 (en) * 1990-08-02 1992-11-06 Rhone Poulenc Chimie N-ALLYLATION REAGENT AND METHOD FOR SYNTHESIS OF N ACYL, N ALLYLANILINE.
ATE160140T1 (en) * 1990-08-02 1997-11-15 Rhone Poulenc Chimie ALLYLATION REAGENT AND A PRODUCTION METHOD USING IT
EP2052612A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
DE102008037629A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
WO2023233367A1 (en) 2022-06-03 2023-12-07 Adama Agan Ltd. Herbicidal mixtures for crop protection

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49134835A (en) * 1973-05-08 1974-12-25

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4701560A (en) * 1985-05-22 1987-10-20 Rhone-Poulenc Specialties Chimiques Process for the preparation of N-2-alkenyl-m-trifluoromethylanilines
US5538985A (en) * 1994-01-27 1996-07-23 Mitsui Toatsu Chemicals, Inc. Pyrrolidinone derivatives
CN114031536A (en) * 2021-12-14 2022-02-11 青海省农林科学院 Pure optical isomer compound for inhibiting weed seed germination and seedling growth and application

Also Published As

Publication number Publication date
NL7603193A (en) 1976-09-30
JPS6011695B2 (en) 1985-03-27
BE839977A (en) 1976-09-24
IT1057396B (en) 1982-03-10
YU80076A (en) 1983-01-21
DE2661042C2 (en) 1989-11-09
AU1241376A (en) 1977-09-29
BG29122A3 (en) 1980-09-15
YU40279B (en) 1985-12-31
CA1076588A (en) 1980-04-29
DK145891C (en) 1983-09-12
NL187313C (en) 1991-08-16
PL100036B1 (en) 1978-08-31
PL102693B1 (en) 1979-04-30
IL49289A0 (en) 1976-05-31
HU179058B (en) 1982-08-28
JPS5289666A (en) 1977-07-27
PH15176A (en) 1982-08-31
AU502662B2 (en) 1979-08-02
FR2305434A1 (en) 1976-10-22
ES446388A1 (en) 1977-10-01
DD126149A5 (en) 1977-06-22
CH625394A5 (en) 1981-09-30
DE2612731A1 (en) 1976-10-07
BR7601774A (en) 1977-10-25
SU942590A3 (en) 1982-07-07
DE2612731C2 (en) 1986-06-26
IL49289A (en) 1979-09-30
DK135776A (en) 1976-09-29
FR2305434B1 (en) 1981-08-07
NL187313B (en) 1991-03-18
IN143281B (en) 1977-10-29
DK145891B (en) 1983-04-05
NZ180424A (en) 1978-03-06
MY8000091A (en) 1980-12-31
BG29135A3 (en) 1980-09-15
MX3355E (en) 1980-10-13

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PE20 Patent expired after termination of 20 years

Effective date: 19960322