GB1122043A - Anilinoalkylcarboxamides and herbicidal compositions containing them - Google Patents
Anilinoalkylcarboxamides and herbicidal compositions containing themInfo
- Publication number
- GB1122043A GB1122043A GB25473/66A GB2547366A GB1122043A GB 1122043 A GB1122043 A GB 1122043A GB 25473/66 A GB25473/66 A GB 25473/66A GB 2547366 A GB2547366 A GB 2547366A GB 1122043 A GB1122043 A GB 1122043A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- atom
- alkyl
- substituted
- hydrogen
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/34—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a carbon skeleton further substituted by nitrogen atoms
Abstract
The invention relates to anilino alkyl-carboxamides of the general formula <FORM:1122043/C2/1> wherein A represents a substituted or unsubstituted alkylene group of 1 to 6 carbon atoms; R1 and R2, which may be the same or different, each represents a hydrogen atom, a substituted or unsubstituted alkyl, aryl or alkenyl group, or a group NR3R4, wherein R3 and R4 each individually represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, provided that both of R1 and R2 are not hydrogen atoms or NR3R4 groups, or R1 and R2 together wit the nitrogen atom to which they are attached form a heterocyclic ring system optionally containing a further hetero atom; X, Y and Z, which may be the same or different, each represents a hydrogen or halogen atom, a cyano or nitro group, a substituted or unsubstituted alkyl or aryl group, an alkylsulphonyl group, or an amino or carbamoyl group or mono- or di-N-alkyl derivatives thereof, provided that not all of X, Y and Z represent hydrogen atoms. Many compounds are claimed per se. The compounds in which at least one of the group X, Y and Z is a strongly electron-withdrawing group may be prepared by reacting a compound of the general formula <FORM:1122043/C2/2> with an amino acid NH2-A-COOH preferably in the presence of a base such as pyridine, sodium or potassium carbonate, bicaronate or hydroxide to give an acid having the general formula <FORM:1122043/C2/3> converting this acid into a corresponding acid chloride, e.g. by reaction with thionyl chloride in the presence of an inert solvent and reacting the acid chloride with an amine HNR1R2, wherein X, Y, Z, A, R1 and R2 are as above, with the proviso that at least one of the groups X, Y and Z is a strongly electron-withdrawing group and hal represents a fluorine, chlorine or bromine atom. The compounds in which none of X, Y or Z represents a strongly electron-withdrawing group are prepared by reacting a compound of a general formula <FORM:1122043/C2/4> with a compound hal-A-COOR5 to give an ester having the formula <FORM:1122043/C2/5> and reacting this ester with an amine HNR1R2, wherein X, Y, Z, A, R1 and R2 have the meanings set forth in claim 1, with the proviso that none of the groups X, Y, Z shall represent a strongly electron-withdrawing group, hal represents a fluorine, chlorine or bromine atom and R5 represents an alkyl group containing 1-4 carbon atoms. In an example, 1-chloro-2,6-dinitrobenzene is reacted with alpha-alanine to produce 2 - (2,6 - dinitroanilino) - propionic acid which is reacted with thionyl chloride to produce the acid chloride which is reacted with methylamine to yield N-methyl-2-(2,6-dinitroanilino) propionamide Many examples are given.ALSO:Herbicidal compositions comprise as active ingredient together with a carrier or surface active agent or both a carrier and surface active agent compounds of the general formula: <FORM:1122043/A5-A6/1> wherein A represents a substituted or unsubstituted alkylene group of 1 to 6 carbon atoms; R1 and R2, which may be the same or different, each represents a hydrogen atom, a substituted or unsubstituted alkyl, aryl or alkenyl group, or a group NR3R4 wherein R3 and R4 each individually represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, provided that both of R1 and R2 are not hydrogen atoms or NR3R4 groups, or R1 and R2 together with the nitrogen atom to which they are attached form a heterocyclic ring system optionally containing a further hetero atom; X, Y and Z, which may be the same or different, each represents a hydrogen or halogen atom, a cyano or nitro group, a substituted or unsubstituted alkyl or aryl group, an alkylsulphonyl group, or an amino or carbamoyl group or mono- or di-N-alkyl derivatives thereof, provided that not all of X, Y and Z represent hydrogen atoms. The compounds may be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions and pastes, Many Examples of active ingredients, carriers and surface active agents are specified.
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB25473/66A GB1122043A (en) | 1966-06-08 | 1966-06-08 | Anilinoalkylcarboxamides and herbicidal compositions containing them |
OA52963A OA02447A (en) | 1966-06-08 | 1967-06-05 | New herbicides, their preparation and use. |
SE07887/67A SE359090B (en) | 1966-06-08 | 1967-06-06 | |
BE699557D BE699557A (en) | 1966-06-08 | 1967-06-06 | |
ES341454A ES341454A1 (en) | 1966-06-08 | 1967-06-06 | Anilinoalkylcarboxamides and herbicidal compositions containing them |
DK296367AA DK118797B (en) | 1966-06-08 | 1967-06-06 | Herbicide. |
FR109222A FR1525715A (en) | 1966-06-08 | 1967-06-06 | New herbicides, their preparation and use |
DE1642337A DE1642337C3 (en) | 1966-06-08 | 1967-06-06 | 2-AryIaminopropionamides and their use as pre-emergence herbicides |
CH795867A CH501358A (en) | 1966-06-08 | 1967-06-06 | Novel herbicides, their preparation and use |
NL6707890.A NL159088B (en) | 1966-06-08 | 1967-06-07 | PROCESS FOR THE PREPARATION OF HERBICIDE PREPARATIONS. |
US855014A US3634509A (en) | 1966-06-08 | 1969-09-03 | 2 6-dinitroanilinoacetamides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB25473/66A GB1122043A (en) | 1966-06-08 | 1966-06-08 | Anilinoalkylcarboxamides and herbicidal compositions containing them |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1122043A true GB1122043A (en) | 1968-07-31 |
Family
ID=10228289
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB25473/66A Expired GB1122043A (en) | 1966-06-08 | 1966-06-08 | Anilinoalkylcarboxamides and herbicidal compositions containing them |
Country Status (9)
Country | Link |
---|---|
BE (1) | BE699557A (en) |
CH (1) | CH501358A (en) |
DE (1) | DE1642337C3 (en) |
DK (1) | DK118797B (en) |
ES (1) | ES341454A1 (en) |
GB (1) | GB1122043A (en) |
NL (1) | NL159088B (en) |
OA (1) | OA02447A (en) |
SE (1) | SE359090B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4243819A (en) * | 1978-02-16 | 1981-01-06 | Zoecon Corporation | Substituted amino acids |
EP0025616A2 (en) * | 1979-08-28 | 1981-03-25 | Shell Internationale Researchmaatschappij B.V. | A method for loosening fruit and/or leaves |
-
1966
- 1966-06-08 GB GB25473/66A patent/GB1122043A/en not_active Expired
-
1967
- 1967-06-05 OA OA52963A patent/OA02447A/en unknown
- 1967-06-06 SE SE07887/67A patent/SE359090B/xx unknown
- 1967-06-06 BE BE699557D patent/BE699557A/xx unknown
- 1967-06-06 DK DK296367AA patent/DK118797B/en unknown
- 1967-06-06 ES ES341454A patent/ES341454A1/en not_active Expired
- 1967-06-06 CH CH795867A patent/CH501358A/en not_active IP Right Cessation
- 1967-06-06 DE DE1642337A patent/DE1642337C3/en not_active Expired
- 1967-06-07 NL NL6707890.A patent/NL159088B/en not_active IP Right Cessation
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4243819A (en) * | 1978-02-16 | 1981-01-06 | Zoecon Corporation | Substituted amino acids |
EP0025616A2 (en) * | 1979-08-28 | 1981-03-25 | Shell Internationale Researchmaatschappij B.V. | A method for loosening fruit and/or leaves |
EP0025616A3 (en) * | 1979-08-28 | 1981-05-06 | Shell Internationale Research Maatschappij B.V. | A method for loosening fruit and/or leaves |
Also Published As
Publication number | Publication date |
---|---|
SE359090B (en) | 1973-08-20 |
DE1642337A1 (en) | 1971-07-29 |
DK118797B (en) | 1970-10-05 |
NL159088B (en) | 1979-01-15 |
DE1642337C3 (en) | 1979-09-27 |
OA02447A (en) | 1970-05-05 |
NL6707890A (en) | 1967-12-11 |
CH501358A (en) | 1971-01-15 |
BE699557A (en) | 1967-12-06 |
ES341454A1 (en) | 1968-12-01 |
DE1642337B2 (en) | 1979-01-18 |
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