GB1008851A - Substituted alpha-haloacetanilides and herbicidal compositions containing them - Google Patents
Substituted alpha-haloacetanilides and herbicidal compositions containing themInfo
- Publication number
- GB1008851A GB1008851A GB3254762A GB3254762A GB1008851A GB 1008851 A GB1008851 A GB 1008851A GB 3254762 A GB3254762 A GB 3254762A GB 3254762 A GB3254762 A GB 3254762A GB 1008851 A GB1008851 A GB 1008851A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- primary
- chlorine
- compounds
- bromine
- 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
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
Abstract
The invention comprises a -haloacetanilides having the generic formula <FORM:1008851/C2/1> selected from the following classes: (1) compounds wherein q is O; m is 1; R1 is a t-alkyl radical; R2 attached in the 6 position is an alkyl radical or an alkoxy radical; and X is chlorine, bromine or iodine; (2) compounds where q is O; R1 is a t-alkyl radical; m is 2; one R2 is primary alkyl or secondary alkyl attached in the 6 position, the other R2 is primary alkyl, secondary alkyl, a chlorine atom or a nitro group attached in the 5 position; and X is chlorine, bromine or iodine; (3) compounds where q is 1; R3 is primary or secondary alkylene, oxaalkylene, alkenylene, or alkynylene; R1 is t-alkyl, m is 1; R2 is alkyl attached in the 6 position; and X is chlorine, bromine or iodine; (4) compounds where q is 0 or 1; R3 is alkylene or alkenylene; m is 2 and the two R2's are taken together with the phenyl group to which they are attached to form a naphthyl group; R1 is a t-alkyl group; and X is chlorine, bromine or iodine; (5) compounds where q is O, R1 is t-alkyl, m is 1 and there is either a halogen atom in the 6 position or a primary or secondary alkyl group in the 5 position, and X is chlorine, bromine or iodine; (6) compounds where q is 1, R3 is alkenylene, m is 1 or 2, R1 is a hydrogen atom, a primary or secondary alkyl radical, or a halogen atom; if there is a substituent in the 6 position it is a primary or secondary alkyl radical; if there is a substituent in the 5 position it is a primary or secondary alkyl radical or a halogen atom; provided that when m is 2 then R1 is a hydrogen atom but not otherwise; and X is a chlorine atom; and (7) compounds where q is O, R1 is a C1-C4 primary or secondary alkyl, m is 1, R2 is a C2 to C4 primary or secondary alkyl attached in the 6 position, provided R1 and R2 have a total of at least 4 carbon atoms; and X is chlorine, bromine or iodine. The compounds may be made by reacting an amine of the formula <FORM:1008851/C2/2> or <FORM:1008851/C2/3> as appropriate with an appropriate haloacetylation agent, preferably either a haloacetic anhydride or a haloacetyl halide. The reaction preferably takes place in a suitable liquid reaction medium such as benzene, diethyl ether, hexane, methylethyl ketone, chlorobenzene, toluene, chloroform and the xylenes. An acid acceptor such as an amine, alkali or alkaline earth hydroxide, carbonate or bicarbonate may also be present. Temperature of 0 DEG to 15 DEG C. are desirable. Specification 781,702 is referred to.ALSO:A herbicidal composition comprises a herbicide adjuvant and an alpha-haloacetanilide of the formula <FORM:1008851/A5-A6/1> the composition being a particulate solid, or a liquid containing a surface-active agent, and the alpha-haloacetanilide being selected from: (1) compounds where q is 0, m is 1, R1 is a t-alkyl, R2 is an alkyl or alkoxy radical in the 6 position, and X is chlorine, bromine or iodine; (2) compounds where q and m are both 0, R1 is a t-alkyl, X is chlorine, bromine or iodine; (3) compounds where q is 0, R1 is t-alkyl, m is 2, there is a primary or secondary alkyl in the 6 position and a primary or secondary alkyl, chlorine atom or nitro group in the 5 position, and X is chlorine, bromine or iodine; (4) compounds where q is 1, R3 is primary or secondary alkylene, oxaalkylene, alkenylene, or alkynylene; R1 is t-alkyl, m is 1, R2 is alkyl in the 6 position, and X is chlorine, bromine or iodine; (5) compounds where q is 0 or 1, R3 is alkylene or alkenylene, m is 2, and the two R2's are taken together with the phenyl group to which they are attached to form a naphthyl group; R1 is a t-alkyl group; and X is chlorine, bromine or iodine; (6) compounds where q is 0, R1 is t-alkyl, m is 1, and thereis either a halogen atom in the 6 position or a primary or secondary alkyl in the 5 position, and X is chlorine, bromine or iodine; (7) compounds where q is 1, R3 is alkylene or alkenylene, m is 1 or 2, R1 is a hydrogen atom, a primary or secondary alkyl, or a halogen atom; any substituent in the 5 position, is a primary or secondary alkyl or a halogen atom, any substituent in the 6 position is a primary or secondary alkyl, provided that when m is 2 then R1 is a hydrogen atom but not otherwise, and X is a chlorine atom; and, (8) compounds where q is 0, R1 is a C1-C4 primary or secondary alkyl, m is 1, R2 is a C2-C4 primary or secondary alkyl in the 6 position, and X is chlorine, bromine or iodine. The herbicidal adjuvants include solid or liquid extending agents such as solvents or diluents, wetting or emulsifying agents and adhesive agents or spreading agents. Examples of liquid and solid extending agents are given, as well as anionic, cationic and non-ionic wetting agents. As solid carriers there may also be employed solid fertilisers such as ammonium nitrate, urea and superphosphate as well as other materials in which plants grow, such as compost, manure, humus and sand. The compositions may be applied as dusts or sprays. Specification 781,702 is referred to.
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13416061A | 1961-08-28 | 1961-08-28 | |
US13416261A | 1961-08-28 | 1961-08-28 | |
US13415861A | 1961-08-28 | 1961-08-28 | |
US13416661A | 1961-08-28 | 1961-08-28 | |
US13416761A | 1961-08-28 | 1961-08-28 | |
US13416161A | 1961-08-28 | 1961-08-28 | |
US13413161A | 1961-08-28 | 1961-08-28 | |
US13415961A | 1961-08-28 | 1961-08-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1008851A true GB1008851A (en) | 1965-11-03 |
Family
ID=27574906
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3254762A Expired GB1008851A (en) | 1961-08-28 | 1962-08-24 | Substituted alpha-haloacetanilides and herbicidal compositions containing them |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE622131A (en) |
BR (1) | BR6242460D0 (en) |
GB (1) | GB1008851A (en) |
NL (1) | NL282569A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4070179A (en) * | 1973-02-07 | 1978-01-24 | Ciba-Geigy Corporation | Plant growth regulation with N-(2-alkoxy-ethyl)-N-chloroacetyl-2,3,6-trimethyl-anilines |
US4284564A (en) * | 1980-03-25 | 1981-08-18 | Monsanto Company | Process for the in-solvent, in-situ generation of haloalkyl alkyl ethers useful to produce N-substituted-2-haloacetanilides |
US4371717A (en) * | 1980-03-25 | 1983-02-01 | Monsanto Company | Process for the in-solvent, in-situ generation of haloalkyl alkyl ethers |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR6567554D0 (en) * | 1964-03-02 | 1973-07-24 | Monsanto Co | N-FORMYL-HALO-ACETANILID HERBICIDES |
US3475155A (en) * | 1964-04-13 | 1969-10-28 | Monsanto Co | Alpha-haloacetanilides as stunting agents |
US3450521A (en) * | 1964-04-20 | 1969-06-17 | Monsanto Co | Herbicidal n-halo-alpha-haloacetanilides |
US3442945A (en) * | 1967-05-22 | 1969-05-06 | Monsanto Co | Phytotoxic alpha-halo-acetanilides |
US3495967A (en) * | 1968-02-07 | 1970-02-17 | Mobil Oil Corp | N-benzothienylchloroacetamides as preemergent herbicides |
US3547620A (en) * | 1969-01-23 | 1970-12-15 | Monsanto Co | N-(oxamethyl)alpha-halo-acetanilide herbicides |
US3630716A (en) * | 1969-09-03 | 1971-12-28 | Monsanto Co | Herbicidal compositions |
US3663200A (en) * | 1969-09-26 | 1972-05-16 | Monsanto Co | Grass selective herbicide composition |
-
0
- NL NL282569D patent/NL282569A/xx unknown
- BE BE622131D patent/BE622131A/xx unknown
-
1962
- 1962-08-24 GB GB3254762A patent/GB1008851A/en not_active Expired
- 1962-08-27 BR BR14246062A patent/BR6242460D0/en unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4070179A (en) * | 1973-02-07 | 1978-01-24 | Ciba-Geigy Corporation | Plant growth regulation with N-(2-alkoxy-ethyl)-N-chloroacetyl-2,3,6-trimethyl-anilines |
US4284564A (en) * | 1980-03-25 | 1981-08-18 | Monsanto Company | Process for the in-solvent, in-situ generation of haloalkyl alkyl ethers useful to produce N-substituted-2-haloacetanilides |
US4371717A (en) * | 1980-03-25 | 1983-02-01 | Monsanto Company | Process for the in-solvent, in-situ generation of haloalkyl alkyl ethers |
Also Published As
Publication number | Publication date |
---|---|
BR6242460D0 (en) | 1973-02-27 |
NL282569A (en) | |
BE622131A (en) |
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