GB922371A - Substituted alpha-halo-or-methoxy-phenylacetic acids, their preparation and use in herbicidal compositions - Google Patents
Substituted alpha-halo-or-methoxy-phenylacetic acids, their preparation and use in herbicidal compositionsInfo
- Publication number
- GB922371A GB922371A GB1427261A GB1427261A GB922371A GB 922371 A GB922371 A GB 922371A GB 1427261 A GB1427261 A GB 1427261A GB 1427261 A GB1427261 A GB 1427261A GB 922371 A GB922371 A GB 922371A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- dichloro
- nitro
- group
- chloro
- 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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- 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
- C07C57/64—Acyl halides
- C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
Abstract
The invention comprises compounds of formula <FORM:0922371/IV(a)/1> wherein X is a chlorine or bromine atom or a methoxy group and each A is a hydrogen, chlorine or bromine atom or a methoxy, nitro, amino or methyl group, at least one of the A's being a halogen atom or a methoxy group and a maximum of two A's being hydrogen except that A is not amino when X is halogen and except that the 2-, 3-, and 5-positions are never occupied simultaneously by chlorine when X is chlorine or methoxy; their esters in which the esterifying group is an unsubstituted alkyl group which contains 1-10 carbon atoms, their alkali metal salts, ammonium salts, amine salts, unsubstituted alkylamine and alkanolamine salts and their amides. The compounds are used in herbicidal composition (see Group VI). The acids are prepared by reacting a benzaldehyde of formula <FORM:0922371/IV(a)/2> with cyanide to form the corresponding a -hydroxybenzylnitrile converting this to the corresponding mandelic acid by treatment with acid and (a) methylating to form the corresponding a -methoxyphenylacetic acid or (b) reacting with phosphorus penta-chloride or bromide to form the corresponding a -chloro-or -bromo-phenylacetic acid. The amino-substituted acids are prepared by reduction of the corresponding nitro compounds. The esters, salts and amides are derived from the acids by conventional procedures. In examples the preparation of the following acids is described: derivatives of a -methoxyphenylacetic acid:-2-methoxy-3,5-dimethyl-or -dichloro-, 2,3,6- or 2,4,5-trichloro-, 2-methyl-4,6-dichloro-, 3-nitro or amino-2,6- or -4,6-dichloro, 3-methoxy-2-chloro-4-or -6-nitro- or -amino-, 2-nitro-3,5-dimethyl-, 4-methoxy-3,5-dichloro-, 3-methoxy-2,4-dichloro-, 3-methoxy- 2,4,6-trichloro-, 3-methoxy-4,6-dibromo-, and 3-methoxy-2-chloro-4-bromo-; derivatives of a -chloro- or -bromo-phenylacetic acid; 2-methoxy-3,5-dimethyl-, 2-methyl-4,6-dichloro-3-nitro-2,6- or -4,6-dichloro-, 2-chloro-3-methoxy- 4-nitro-, 2-nitro-3,5-dimethyl, 3,5-dichloro-4-methoxy-, 2,4-dichloro- 3-methoxy-, 2-methoxy- 3,5-dichloro-, 3-methoxy-2,4,6-trichloro-, 2,4,5-trichloro-, 3-methoxy-4,6-dibromo- and 2-chloro-3-methoxy-4-bromo-; derivatives of a -chloro-phenylacetic acid:- 2,3,6-trichloro-and 2-chloro-3-methoxy-6-nitro-; and a -bromo- 2,3,5-trichlorophenylacetic acid. Several intermediate mandelic acids are described in examples. The following derivatives of the acids are also described in examples:-sodium, ammonium, dimethylamine, diethanolamine and morpholine salts; ethyl, n-butyl and n-decyl esters; acid chloride, amide, N-n-decylamide and N:N-diethylamide.ALSO:Herbicidal composition contain as active ingredient a compound of formula <FORM:0922371/VI/1> wherein X is a chlorine or bromine atom or a methoxy group and each A is a hydrogen, chlorine or bromine atom or a methoxy, nitro, amino or methyl group, at least one of the A's being a halogen atom or a methoxy group and a maximum of two A's being hydrogen except that A is not amino when X is halogen and except that the 2-, 3- and 5-positions are never occupied simultaneously by chlorine when X is chlorine or methoxy; its esters in which the esterifying group is an unsubstituted alkyl group containing 1-10 carbon atoms, its alkali metal salts, its ammonium salt, its amine salts, its unsubstituted alkylamine and alkanolamine salts and its amides (see Group IV (b)). The compositions may be dusts using talcs or clays as diluent, solutions in xylene, kerosene, methylnaphtha-lene or water or suspensions or emulsions in water. In examples: (1) emulsifiable concentrates are prepared by mixing (a) a ,2,3,6-tetrachlorophenylacetic acid, methanol and a non-ionic detergent or (b) n-butyl a ,2,3,6-tetrachlorophenyl-acetate, xylene, kerosene and a non-ionic emulsifier; (2) talc and sodium a ,4,6-trichloro-2-methyl-phenylacetate are mixed to form a dust composition.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2917260A | 1960-05-16 | 1960-05-16 | |
US3253560A | 1960-05-31 | 1960-05-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB922371A true GB922371A (en) | 1963-03-27 |
Family
ID=26704628
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1427261A Expired GB922371A (en) | 1960-05-16 | 1961-04-20 | Substituted alpha-halo-or-methoxy-phenylacetic acids, their preparation and use in herbicidal compositions |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH456561A (en) |
GB (1) | GB922371A (en) |
NL (1) | NL264389A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113336636A (en) * | 2021-05-25 | 2021-09-03 | 湖州柏特生物科技有限公司 | High-yield synthesis process of DL-mandelic acid |
-
0
- NL NL264389D patent/NL264389A/xx unknown
-
1961
- 1961-04-20 GB GB1427261A patent/GB922371A/en not_active Expired
- 1961-05-03 CH CH517361A patent/CH456561A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113336636A (en) * | 2021-05-25 | 2021-09-03 | 湖州柏特生物科技有限公司 | High-yield synthesis process of DL-mandelic acid |
CN113336636B (en) * | 2021-05-25 | 2023-11-10 | 湖州柏特生物科技有限公司 | Synthesis process of DL-mandelic acid with high yield |
Also Published As
Publication number | Publication date |
---|---|
NL264389A (en) | |
CH456561A (en) | 1968-07-31 |
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