[go: up one dir, main page]

GB1021014A - Novel herbicidal compounds and compositions - Google Patents

Novel herbicidal compounds and compositions

Info

Publication number
GB1021014A
GB1021014A GB2868063A GB2868063A GB1021014A GB 1021014 A GB1021014 A GB 1021014A GB 2868063 A GB2868063 A GB 2868063A GB 2868063 A GB2868063 A GB 2868063A GB 1021014 A GB1021014 A GB 1021014A
Authority
GB
United Kingdom
Prior art keywords
dichlorophenyl
group
acid
carbon atoms
general 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
GB2868063A
Inventor
John Yates
Sidney Edward Callander
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.)
Shell Research Ltd
Original Assignee
Shell Research 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 Shell Research Ltd filed Critical Shell Research Ltd
Priority to GB2868063A priority Critical patent/GB1021014A/en
Priority to NL6408190A priority patent/NL6408190A/xx
Priority to BR16092964A priority patent/BR6460929D0/en
Priority to FR982065A priority patent/FR1406171A/en
Priority to BE650701D priority patent/BE650701A/xx
Priority to DE1964S0092114 priority patent/DE1290536B/en
Priority to CH940564A priority patent/CH447707A/en
Priority to DK359464A priority patent/DK110029C/en
Publication of GB1021014A publication Critical patent/GB1021014A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings

Landscapes

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

Abstract

The invention relates to compounds of the general formula <FORM:1021014/C2/1> wherein Y represents a chlorine or bromine atom and R represents an alkyl or alkenyl group of 1-10 carbon atoms, n is 1-5, and Z is a CN group, a CONHR1 or CONR1R2 group wherein R1 and R2 is an alkyl group of 1-10 C atoms, or a COOR3 group wherein R3 represents a hydrogen atom, an alkali metal, an ammonium or a substituted ammonium group, or an alkyl group of 1-10 carbon atoms; excluding the compounds 2 - (2 - chlorophenyl) - propionitrile, 2 - (4 - chlorophenylpropionic acid), 2 - (2,4-dichlorophenyl) -propionic acid, and 2 - (3,4-dichlorophenyl)-propionic acid. Illustrative of many compounds claimed per se are 2-(4-bromophenyl) - N,N - dimethylpropionamide, 2 - (2,4 - dichlorophenyl) - N,N - dimethylbutyramide, 2 - (2,3,6 - trichlorophenyl) - N,N-dimethylpropionamide, 2 - (4 - chlorophenyl) propionitrile, 2 - (2,4 - dichlorophenyl) pentanonitrile, 2 - (2,4 - dichlorophenyl) - 4 - pentenonitrile, 2 - (2,3 - dichlorophenyl) propionic acid, 2 - (2,4 - dichlorophenyl) pentanoic acid, 2 - (2,4 - dichlorophenyl) - 4 - pentenoic acid. The amides are prepared by reacting an acid chloride of the general formula <FORM:1021014/C2/2> where Y R and n are as indicated above with an amine of the general formula HNR1R2 or HNR1H wherein R1 and R2 are as indicated above, under anhydrous or substantially anhydrous conditions. The nitriles are prepared by reacting in an inert solvent a halogen substituted phenyl acetonitrile having the general formula <FORM:1021014/C2/3> wherein Y and n are as indicated above, with an alkyl halide or an alkenyl halide having the formula RX, wherein R is as indicated above and X is a halogen atom, in the presence of a basic alkylation catalyst e.g. sodium amide or sodium hydride. The acids are prepared by hydrolysing a nitrile having the general formula <FORM:1021014/C2/4> wherein R Y and n are as indicated above. Many examples are given.ALSO:Herbicidal compositions comprise active ingredient one or more compounds having the formula <FORM:1021014/A5-A6/1> wherein Y represents a chlorine or bromine atom and R represents an alkyl or alkenyl group of 1-10 carbon atoms, n is 1-5, and Z represents a CN group, a CONHR1 or CONR1R2 group where R1 and R2 represent an alkyl group of 1-10 carbon atoms, or a COOR3 group wherein R3 represents a hydrogen atom, an alkali metal, an ammonium or a substituted ammonium group, or an alkyl group of 1-10 carbon atoms; together with a carrier and/or surface active agent. Many solid and liquid carriers are specified. The composition may contain other ingredients e.g. conditioning agents such as sodium polyphosphate, cellulose ethers or ethylene diamine tetra acetic acid other herbicides pesticides or stickers wetting and emulsifying agents. Many active ingredients are specified among them 2-(4-Bromophenyl)-N, N-dimethylpropionamide, 2-(2, 4-Dichlorophenyl)-N, N-dimethylbutyramide, 2-(2, 3, 6-Trichlorophenyl)-N, N-dimethylpropionamide, 2-(4-Chlorophenyl) propionitrile, 2-(2, 4-Dichlorophenyl) pentanonitrile, 2-(2, 4-Dichlorophenyl)-4-pentenonitrile, 2-(2, 3-Dichlorophenyl) propionic acid, 2-(2, 4-Dichlorophenyl) pentanoic acid, 2-(2, 4-Dichlorophenyl)-4-pentenoic acid.
GB2868063A 1963-07-19 1963-07-19 Novel herbicidal compounds and compositions Expired GB1021014A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB2868063A GB1021014A (en) 1963-07-19 1963-07-19 Novel herbicidal compounds and compositions
NL6408190A NL6408190A (en) 1963-07-19 1964-07-17
BR16092964A BR6460929D0 (en) 1963-07-19 1964-07-17 HERBICIDAL COMPOSITIONS AND PROCESS OF PREPARATION OF THE RESPECTIVE ACTIVE COMPOUNDS
FR982065A FR1406171A (en) 1963-07-19 1964-07-17 New compounds and new herbicidal compositions
BE650701D BE650701A (en) 1963-07-19 1964-07-17
DE1964S0092114 DE1290536B (en) 1963-07-19 1964-07-17 Chlorine or bromophenylpropionic acid amide compounds and their use as a pre-emergence herbicide
CH940564A CH447707A (en) 1963-07-19 1964-07-17 Herbicidal agent
DK359464A DK110029C (en) 1963-07-19 1964-07-20 Herbicide and process for the preparation of halophenylalkyl derivatives for use therein.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2868063A GB1021014A (en) 1963-07-19 1963-07-19 Novel herbicidal compounds and compositions

Publications (1)

Publication Number Publication Date
GB1021014A true GB1021014A (en) 1966-02-23

Family

ID=10279438

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2868063A Expired GB1021014A (en) 1963-07-19 1963-07-19 Novel herbicidal compounds and compositions

Country Status (7)

Country Link
BE (1) BE650701A (en)
BR (1) BR6460929D0 (en)
CH (1) CH447707A (en)
DE (1) DE1290536B (en)
DK (1) DK110029C (en)
GB (1) GB1021014A (en)
NL (1) NL6408190A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4132728A (en) 1976-08-16 1979-01-02 Shell Oil Company Preparation of nitriles

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EG11383A (en) * 1972-07-11 1979-03-31 Sumitomo Chemical Co Novel composition for controlling nixious insects and process for preparing thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1245091A (en) * 1958-12-31 1960-11-04 Du Pont Pesticide compositions, in particular herbicides, based on polychlorophenylacetic acids or on compounds of these acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4132728A (en) 1976-08-16 1979-01-02 Shell Oil Company Preparation of nitriles

Also Published As

Publication number Publication date
BR6460929D0 (en) 1973-08-07
NL6408190A (en) 1965-01-20
BE650701A (en) 1965-01-18
CH447707A (en) 1967-11-30
DE1290536B (en) 1969-03-13
DK110029C (en) 1968-08-26

Similar Documents

Publication Publication Date Title
GB862226A (en) 2-oxo-benzthiazoline derivatives and herbicidal compositions containing them
GB1039442A (en) Imino-thiadiazolines and their use as agents for combating pests
GB1033163A (en) New diphenylethers and herbicidal preparations containing them
GB1116693A (en) Novel cyanoalkylhydrazines
GB1021014A (en) Novel herbicidal compounds and compositions
GB869169A (en) New n-aryl-alkanamides, their preparation and use as herbicides
KR970705551A (en) PROCESS FOR PRODUCING QUATERNARY GLYCINE NITRILES
US3890352A (en) Dioxolanyl carbonyl carboxamides
GB955287A (en) Herbicides and methods of using same
GB1398201A (en) N-sulphenylated carbamidoximes a process for their preparation and their fungicidal and bactericidal use
GB1086339A (en) Herbicides
GB885043A (en) New disubstituted anilides and herbicidal compositions containing them
GB1122043A (en) Anilinoalkylcarboxamides and herbicidal compositions containing them
GB1018308A (en) Novel dichlorophenyl-substituted amides,thioamides,imidates and amidines,and herbicidal compositions containing them
GB1062680A (en) New urea derivatives,the manufacture thereof,selective herbicides containing the same and application of said herbicides
GB951886A (en) Aminoethyl sulfonic acid esters and fungicidal compositions containing same
GB1020809A (en) Unsaturated phosphoric acid esters and their use as pest-control agents
GB1020065A (en) Insecticidal 5-halo-3-phenylsalicylanilides and their use
US3502726A (en) Hydrazine derivatives of oligomers of tetrafluoroethylene and hexafluoropropene
GB1095726A (en) Amino-azido-triazines, and their use as plant growth regulants
GB1038184A (en) New n-monoalkoxy amides of substituted phenoxy alkanoic acids, herbicidal compositions and process for preparing said amides
ES275121A1 (en) Herbicidal method
GB1094882A (en) Phenylamine ammonium salts
GB1088224A (en) Acetamidine derivatives
GB1035177A (en) Compositions for destroying or preventing the growth of water plants