GB877067A - Improvements in or relating to alkyldichlorobenzoic acids and their use as herbicides - Google Patents

Improvements in or relating to alkyldichlorobenzoic acids and their use as herbicides

Info

Publication number
GB877067A
GB877067A GB1753259A GB1753259A GB877067A GB 877067 A GB877067 A GB 877067A GB 1753259 A GB1753259 A GB 1753259A GB 1753259 A GB1753259 A GB 1753259A GB 877067 A GB877067 A GB 877067A
Authority
GB
United Kingdom
Prior art keywords
dichloro
acid
acids
methyl
mixture
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
Application number
GB1753259A
Inventor
David Xavier Klein
Theodore Alsdorf Girard
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Heyden Newport Chemical Corp
Original Assignee
Heyden Newport Chemical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Heyden Newport Chemical Corp filed Critical Heyden Newport Chemical Corp
Publication of GB877067A publication Critical patent/GB877067A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
    • C07C63/70—Monocarboxylic acids
    • 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
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof

Abstract

The invention comprises 2,3-dichloro-6-methylbenzoic acid and its salts and a mixture of methyldichlorobenzoic acids resulting from the conversion of one methyl group of dichloro-o-xylene to a carboxyl group. The compounds may be prepared by ring-chlorinating o-xylene, side-chain chlorinating the resulting isomeric mixture of dichloro-o-xylenes to give a mixture of methyldichlorobenzyl chloride isomers, esterifying the chloride with an alkali metal salt of a saturated monocarboxylic acid e.g. formic acid, to give a mixture of methyldichlorobenzyl esters of the acid and oxidising the ester e.g. with nitric acid, to give the desired mixture of acids. The 2,3-dichloro-6-methyl isomer may be separated from the mixture by selective esterification, followed by hydrolysis, leaving a residue containing the 2-methyl-3,6-dichloro, 2-methyl-3,4-dichloro and 2-methyl-4,5-dichloro isomers. Alkyldichlorobenzoic acids of the formula <FORM:0877067/IV (b)/1> where one of R and R1 is a chlorine atom and the other is an alkyl group containing up to 4 carbon atoms, and their salts, amides and aliphatic monohydric alcohol esters, which may be used in herbicidal compositions, are mentioned. The acids may be prepared by oxidising a bromodichlorotoluene to the benzoic acid and then replacing the bromine atom by an alkyl group according to the Fittig reaction or by subjecting a bromodichloroalkylbenzene to a Grignard reaction.ALSO:An herbicidal composition comprises an inert carrier and a herbicidally effective amount of an alkyldichlorobenzoic acid of the formula <FORM:0877067/VI/1> where one of R and R1 is a chlorine atom and the other is an alkyl group containing up to 4 carbon atoms, or a salt, amide or aliphatic monohydric alcohol ester of the acid. The composition may take the form of a dust or powder, an aqueous dispersion, an oil-in-water emulsion or a solution in a ketone, alcohol, ether or hydrocarbon. The composition preferably contains 2,3-dichloro-6-methyl benzoic acid and may contain other isomeric methyldichlorobenzoic acids.
GB1753259A 1959-05-21 1959-05-22 Improvements in or relating to alkyldichlorobenzoic acids and their use as herbicides Expired GB877067A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEH0036435 1959-05-21

Publications (1)

Publication Number Publication Date
GB877067A true GB877067A (en) 1961-09-13

Family

ID=7153009

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1753259A Expired GB877067A (en) 1959-05-21 1959-05-22 Improvements in or relating to alkyldichlorobenzoic acids and their use as herbicides

Country Status (2)

Country Link
DE (1) DE1417413A1 (en)
GB (1) GB877067A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3280174A (en) * 1961-05-15 1966-10-18 Hooker Chemical Corp Mixtures of dihalo-o-tolylacetic acids and derivatives
US3336131A (en) * 1966-09-26 1967-08-15 Hooker Chemical Corp Method of controlling plant growth

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3280174A (en) * 1961-05-15 1966-10-18 Hooker Chemical Corp Mixtures of dihalo-o-tolylacetic acids and derivatives
US3336131A (en) * 1966-09-26 1967-08-15 Hooker Chemical Corp Method of controlling plant growth

Also Published As

Publication number Publication date
DE1417413A1 (en) 1969-09-04

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