GB1067034A - Halogenated alkoxyalkoxybenzonitriles - Google Patents
Halogenated alkoxyalkoxybenzonitrilesInfo
- Publication number
- GB1067034A GB1067034A GB3865263A GB3865263A GB1067034A GB 1067034 A GB1067034 A GB 1067034A GB 3865263 A GB3865263 A GB 3865263A GB 3865263 A GB3865263 A GB 3865263A GB 1067034 A GB1067034 A GB 1067034A
- Authority
- GB
- United Kingdom
- Prior art keywords
- denotes
- formula
- compounds
- effected
- carbon atoms
- 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
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula <FORM:1067034/C2/1> in which R1 denotes a straight or branched chain alkyl or alkenyl group of 1-18 carbon atoms, R2 denotes hydrogen or a straight or branched chain alkyl or alkenyl group of 1-18 carbon atoms, X1 denotes a halogen atom and X2 denotes a halogen atom or a nitro group. The compounds may be prepared by reacting a metallic salt of a phenol of the formula <FORM:1067034/C2/2> in which M denotes a metal, with an alkoxyalkyl halide of the formula R1OCH(R2)Halogen. Alternatively, the compounds may be prepared by halogenating a corresponding unhalogenated or monohalogenated compound. Halogenation may be effected with elementary halogen, or chlorination may be effected with a mixture of sulphur monochloride, sulphuryl chloride and aluminium chloride, or bromation may be effected with sodium or potassium hypobromite, or iodination may be effected with iodine monochloride or with an alkali-metal iodide and an oxidizing agent. The halogenation may be effected in two stages, and different halogens may be introduced in each stage. As a further alternative, the compounds may be prepared by treating an oxime of the formula <FORM:1067034/C2/3> by known methods for the conversion of oximes to nitriles. An example is given of the preparation of 3,5 - diiodo - 4 - methoxymethoxybenzonitrile by reacting 3,5-diiodo-4-hydroxybenzonitrile sodium salt with monochlorodimethyl ether in tetramethylene sulphone. Other products similarly obtainable are 3,5-dichloro- and 3,5 - dibromo - 4 - methoxymethoxybenzonitrile, 3,5 - diiodo - 4 - n - octyloxymethoxybenzonitrile, and 3 - iodo - 4 - methoxymethoxy - 5 - nitrobenzonitrile. Reference is made also to the production of a 3-chloro-5-bromo-benzonitrile derivative of Formula I. The products are useful as herbicides (see Division A5). Oximes of Formula III above are obtainable from hydroxylamine and the corresponding benzaldehyde derivatives, which are themselves obtainable by treating a metallic derivative of the corresponding 4-hydroxybenzaldehyde with an alkoxyalkyl halide. n-Octyloxymethyl chloride, used in the preparation of one of the products of the example, is prepared by treating a mixture of n-octyl alcohol and paraformaldehyde with dry hydrogen chloride.ALSO:As selective herbicides, use is made of compounds of the formula <FORM:1067034/A5-A6/1> in which R1 denotes a straight or branched chain alkyl or alkenyl group of 1-18 carbon atoms, R2 denotes hydrogen or a straight or branched chain alkyl or alkenyl group of 1-18 carbon atoms, X1 denotes a halogen atom and X2 denotes a halogen atom or a nitro group (see Division C2). The compounds may be formulated as wettable powders, granules, solutions or emulsions, including self-emulsifiable concentrates, or aerosol preparations with the aid of solid or liquid diluents, carriers, or ionic or non-ionic surface-active agents, a number of each of which are specified. The compositions may include other herbicides, particularly those of the phenoxyalkanoic acid type. The use of the compositions for controlling annual broad-leafed weeds and for destroying potato haulms is stressed. Examples are given.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3865263A GB1067034A (en) | 1963-10-01 | 1963-10-01 | Halogenated alkoxyalkoxybenzonitriles |
CH1249764A CH431188A (en) | 1963-10-01 | 1964-09-25 | Herbicidal composition |
BE653677A BE653677A (en) | 1963-10-01 | 1964-09-28 | |
NL6411390A NL6411390A (en) | 1963-10-01 | 1964-09-30 | |
FR990042A FR1440627A (en) | 1963-10-01 | 1964-10-01 | New herbicides |
BE684247D BE684247A (en) | 1963-10-01 | 1966-07-15 | |
NL6610042A NL6610042A (en) | 1963-10-01 | 1966-07-15 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3865263A GB1067034A (en) | 1963-10-01 | 1963-10-01 | Halogenated alkoxyalkoxybenzonitriles |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1067034A true GB1067034A (en) | 1967-04-26 |
Family
ID=10404834
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3865263A Expired GB1067034A (en) | 1963-10-01 | 1963-10-01 | Halogenated alkoxyalkoxybenzonitriles |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE653677A (en) |
CH (1) | CH431188A (en) |
GB (1) | GB1067034A (en) |
NL (1) | NL6411390A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4637830A (en) * | 1981-04-24 | 1987-01-20 | Ciba-Geigy Corporation | Herbicidal concentrates |
-
1963
- 1963-10-01 GB GB3865263A patent/GB1067034A/en not_active Expired
-
1964
- 1964-09-25 CH CH1249764A patent/CH431188A/en unknown
- 1964-09-28 BE BE653677A patent/BE653677A/xx unknown
- 1964-09-30 NL NL6411390A patent/NL6411390A/xx unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4637830A (en) * | 1981-04-24 | 1987-01-20 | Ciba-Geigy Corporation | Herbicidal concentrates |
Also Published As
Publication number | Publication date |
---|---|
BE653677A (en) | 1965-03-29 |
NL6411390A (en) | 1965-04-02 |
CH431188A (en) | 1967-02-28 |
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