Preparation and Reactions of Several Chlorine Substituted Phenoxyacetyl Chlorides

Hill, Carl M.; Towns, Myron B.; Senter, Gilbert W.

doi:10.1021/ja01169a065

Cited by 8 publications

(4 citation statements)

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“…The other amides were prepared by refiuxing equimolar quantities of the corresponding acid chloride (Hill, Towns & Senter, 1949) and 3,4-dicbloroaniline in 200 ml of chlorobenzene. Tbe reaction was continued until the evolution of hydrochloric acid had stopped [c. 6 hours).…”

Section: Methods Bmentioning

confidence: 99%

The Herbicidal Effect of Some Substituted Anilides

Matolcsy

Hamrán

1964

Weed Research

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The 3,4-dichloroanilides of four herbicidally active and of four inactive or weakly active phenoxyalkanecarboxylic acids were synthesized and tested for herbicidal activity, in order to study the effect of compounds comprising the two characteristic groupings within one molecule. 4-Chloro-2-methylphenoxyacetic acid, 2,4-dichlorophenoxyacetic acid, 2,4,5-trichlorophenoxyacetic acid and a- [2,4,5-trichlorophenoxy] propionic acid were selected as representatives of active compounds; and phenoxyacetic acid, 2-methylphenoxyacetic acid, 3,5-dichlorophenoxyacetic acid and 2,4,6-trichlorophenoxyacetic acid as inactive or weakly active compounds.The compounds were tested in the glasshouse on wheat and white mustard as preand post-emergence treatments. The synthesized 3,4-dichloroanilides had no or little herbicidal activity, as compared with the high activity of the known herbicides 3,4dichloropropionanilide and 2,4-dichlorophenoxyacetic acid. The conclusion can be drawn that the introduction of phenoxy groupings into the acid moiety of the active fatty acid-3,4-dichloroanilides as well as the introduction of the 3,4-dichloroaniline group into the carboxylic group of the active phenoxyacetic acids decreases herbicidal activity. This last phenomenon is probably due to a decreased ability to be hydrolysed. L'activite herbicide de quelques anilides substitueesR£sum£. Les 3,4-dichloranilides de huit acides ph^noxyalkylcarboxyliques (quatre poss^dant une activity herbicide, et quatre inactifs ou faiblement actifs) on ^t^ synthdtis^s et soumis a des tests herbicides dan le but d'etudier les effets de composes comprenant les deux groupements caract^ristiques dans leur molecule.Les acides 2-m^thyl-4-chloroph^noxyac^tique, 2,4,5-trichloroph^noxyac6tique et 2,4,5trichlorophinoxypropionique ont 6tt choisis comme repr^sentants des composes actifs; les acides ph6noxyac6tique,2-m6thylph^noxyac6tique,3,5-dichloroph^noxyac^tiqueet 2,4,6-trichloroph^noxyacitique, comme repr^sentants des composes inactifs ou faiblement actifs.Les essais ont ix.€ effectu^s en serre sur bl6 et moutarde blanche, en application de pr6 et de post-6mergence. Les 3,4-dichloroanilides synth6tis6es ne manifest^rent que peu ou pas d'activit^ herbicide en comparaison des composes actifs connus, tels que la 3,4dichloropropionanilide et I'acide 2,4-dichloroph^noxyac6tique. On peut en deduire la conclusion suivante: l'introduction du groupe 3,4-dichloropropionanilide dans le groupe carboxylique des acides ph^noxyac^tiques actifs diminue leur activity herbicide. Le ph^nomene est probablement du a une diminution de leur possibility d'hydrolyse. Die herbizide Wirksamkeit substituierter Anilide Zusammenfassung. Die 3,4-Dichloranilide von vier herbizid-aktiven und vier nicht bzw. weitgehend nicht aktiven Phenoxyfettsauren wurden synthetisiert und auf ihre herbizide Wirksamkeit gepruft, um die Wirkung von Substanzen, die diese beiden charakteristischen Gruppen im Molekul vereinigen, zu untersuchen. 2-Methyl-4chlorphenoxyessigsaure, 2,4,5-Trichlorphenoxyessigsaure und a-[2,4...

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Section: Methods Bmentioning

confidence: 99%

The Herbicidal Effect of Some Substituted Anilides

Matolcsy

Hamrán

1964

Weed Research

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“…Chloride (2,4,5-T-Cl). 2,4,5-T-Cl was prepared according to Hill et al (1949) and modifications by Wood and Fontaine (1952). 2,4,5-T (0.1 mol, recrystallized from benzene) was placed in a round-bottom flask equipped with a condenser and thionyl chloride (0.3 mol) was added.…”

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confidence: 99%

2,4,5-Trichlorophenoxyacetic acid. Synthesis and thin-layer chromatography properties of amino acid conjugates and gas-liquid chromatography and mass spectra of methyl ester derivatives

Arjmand¹,

Hamilton²,

Mumma³

1978

J. Agric. Food Chem.

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“…Physical Properties, Yields, and Analytical Data for Amide Derivatives of Halogenated Phenoxy Acids Recrystallized once or more from ethyl alcohol water and ethyl acetate-petroleum ether unless otherwise indicated 6. Recrystallized from ethyl alcohol water only.…”

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confidence: 99%