ES341454A1 - Anilinoalkylcarboxamides and herbicidal compositions containing them - Google Patents
Anilinoalkylcarboxamides and herbicidal compositions containing themInfo
- Publication number
- ES341454A1 ES341454A1 ES341454A ES341454A ES341454A1 ES 341454 A1 ES341454 A1 ES 341454A1 ES 341454 A ES341454 A ES 341454A ES 341454 A ES341454 A ES 341454A ES 341454 A1 ES341454 A1 ES 341454A1
- Authority
- ES
- Spain
- 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
- 230000002363 herbicidal effect Effects 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 3
- 239000004094 surface-active agent Substances 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- KLNIWDWRMUMRQA-UHFFFAOYSA-N 2-(2,6-dinitroanilino)propanoic acid Chemical compound OC(=O)C(C)NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O KLNIWDWRMUMRQA-UHFFFAOYSA-N 0.000 abstract 1
- BPPMIQPXQVIZNJ-UHFFFAOYSA-N 2-chloro-1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1Cl BPPMIQPXQVIZNJ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- -1 dusts Substances 0.000 abstract 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000006072 paste Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940080818 propionamide Drugs 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
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
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 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.
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 |
|---|---|
| ES341454A1 true ES341454A1 (en) | 1968-12-01 |
Family
ID=10228289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES341454A Expired ES341454A1 (en) | 1966-06-08 | 1967-06-06 | 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) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4243819A (en) * | 1978-02-16 | 1981-01-06 | Zoecon Corporation | Substituted amino acids |
| EP0025616B1 (en) * | 1979-08-28 | 1983-11-30 | Shell Internationale Researchmaatschappij B.V. | A method for loosening fruit and/or leaves |
| SG11202112906TA (en) * | 2019-06-11 | 2021-12-30 | Fortephest Ltd | Novel non-coding heterocyclic amino acids (nchaa) and their use as herbicides |
-
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 DK DK296367AA patent/DK118797B/en unknown
- 1967-06-06 ES ES341454A patent/ES341454A1/en not_active Expired
- 1967-06-06 BE BE699557D patent/BE699557A/xx unknown
- 1967-06-06 CH CH795867A patent/CH501358A/en not_active IP Right Cessation
- 1967-06-06 DE DE1642337A patent/DE1642337C3/en not_active Expired
- 1967-06-06 SE SE07887/67A patent/SE359090B/xx unknown
- 1967-06-07 NL NL6707890.A patent/NL159088B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK118797B (en) | 1970-10-05 |
| NL159088B (en) | 1979-01-15 |
| DE1642337B2 (en) | 1979-01-18 |
| SE359090B (en) | 1973-08-20 |
| NL6707890A (en) | 1967-12-11 |
| DE1642337C3 (en) | 1979-09-27 |
| OA02447A (en) | 1970-05-05 |
| BE699557A (en) | 1967-12-06 |
| DE1642337A1 (en) | 1971-07-29 |
| GB1122043A (en) | 1968-07-31 |
| CH501358A (en) | 1971-01-15 |
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