Fruit Drop Control, Evaluation of Chlorine-Substituted Phenoxyacetic Acids and Amides for Retarding Abscission of Apple Fruits

Marth, Paul C.; Audia, William V.; Mitchell, James W.

doi:10.1021/jf60096a007

Cited by 2 publications

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“…In view of the well known sensitivity of biological specimens to very small concentrations of impurities, amide production may be of some importance for those herbicidal formulations containing amine salts which have been subjected to temperatures above 80°d uring manufacture. The biological effects of 2,4-D amides have been studied (Krewson et al, 1959;Marth et al, 1959;Preston et al, 1958), and it has been concluded that the "presence of an amide group on the side chain of chlorinated phenoxy plant regulators is perhaps almost as important as the position and degree of chlorination on the benzene nucleus'' (Marth et al, 1959).…”

Section: Resultsmentioning

confidence: 99%

Pyrolysis of some amine salts of 2,4-dichlorophenoxyacetic acid

Ss¹,

Rg²

1974

J. Agric. Food Chem.

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was undertaken.Reagents. Commercial solid n-tetradecyl-and n-dodecylamines (Aldrich) and liquid n-butylamine were purified by vacuum distillation. Reagent grade dimethylamine (Eastman) was used without further purification. A 20% aqueous solution of methylamine was used for the preparation of the methylamine salt. Commercial 2,4-D (Aldrich) was recrystallized from benzene until a constant melting point of 140.3 ± 0.5°was attained.1:1 salts of 2,4-D were made by adding stoichiometric amounts of the amines dissolved in benzene-acetone solutions to solid 2,4-D at 10°. The solutions were shaken until all the 2,4-D had disappeared. The solvent was removed under vacuum at room temperature. The resultant salts were recrystallized from 1:1:1 ether-acetone-hexane until the melting points were constant.EXPERIMENTAL SECTION Pyrolysis Experiments. The solid salts were pyrolyzed in sealed Pyrex tubes covered with aluminum foil. Separate samples were pyrolyzed for 1 hr at temperatures from 30 to 200°. The tubes were then cooled before recording mass, infrared, and nuclear magnetic spin resonance spectra of the products.

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Section: Resultsmentioning

confidence: 99%