Plant Growth Regulators, Synthesis and Biological Activity of Some Quaternary Ammonium and Related Compounds That Suppress Plant Growth

Krewson, C. F.; Wood, John; Wolfe, Winthrop C; Mitchell, John W.; Marth, Paul C.

doi:10.1021/jf60098a007

Cited by 21 publications

(7 citation statements)

References 2 publications

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“…3 In addition, the published literature since then has described a multitude of uses for quat salts, 4 including preparation of ionic liquids, 5 antimicrobial agents, 6 disinfectants, 7 surfactants, 8 fabric soeners, 9 antistatic agents, 10 wood preservation, 11 osmolytes, 12 chemical capacitors, 13 electrolytes for batteries, 14 capping agents for copper nanoparticles, 15 and plant growth retardants. 16 Quaternary ammonium compounds are typically prepared by quaternization of tertiary amines with alkyl halides and by anion exchange reactions on commercially available salts. 17 Such a synthetic route poses a limit on the variety of quat salt structures based on availability of amines and alkyl halides.…”

Section: Introductionmentioning

confidence: 99%

A simple and rapid route to novel tetra(4-thiaalkyl)ammonium bromides

et al. 2013

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A simple approach for the preparation of symmetrical quaternary ammonium bromides employing thiolene click chemistry is used to synthesize tetra(4-thiaalkyl)ammonium bromides. This approach allows the incorporation of a variety of alkyl moieties onto the nitrogen center with a one-step synthesis involving easy work-up, no side reactions and environmentally friendly reagents. To elucidate information regarding the behaviour of this novel class of compounds, comparisons to tetraalkylammonium analogues have been made. These include melting points, activity as phase-transfer catalysts, and conformational predictions from computational modelling. All results are consistent in indicating stronger bonding between the quaternary cation and the anion for the salts with 4-thiaalkyl chains as compared to those with n-alkyl chains.

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Section: Introductionmentioning

confidence: 99%

A simple and rapid route to novel tetra(4-thiaalkyl)ammonium bromides

et al. 2013

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“…One of the most active compounds was a quaternary ammonium carbamate, designated Amo-1618 (4-hydroxyl-5isopropyl -2 -methylphenyltrimethylammonium chloride, 1-piperidine carboxylate), prepared from the terpene thymol by R. L. Shriner at the University of Illinois. Much work has been done on the synthesis and testing of derivatives of Amo-1618 (Krewson et al, 1959). Knight et al (1969) have studied the influence on plant growth-retardant activity of various substituents of aryl quaternary ammonium, phosfonium, and sulfonium compounds.…”

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confidence: 99%

Effect of phenyl substitutents in benzyl quaternary ammonium derivatives of (+)-limonene on plant growth-retardant activity

Newhall¹

1971

J. Agric. Food Chem.

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The growth-retardant activity of 26 benzyl quaternary ammonium derivatives of (+)-limonene was evaluated using two bioassays, one based on the root growth of cucumber seed and the other on total fresh weight increase of alfalfa seeds exposed to dilute aqueous solutions of each compound. Inhibition of human blood serum cholinesterase was also determined manometrically. A highly significant correlation between serum cholinesterase inhibition and plant growth retardation found for 24 compounds on cucumber and 22 compounds on alfalfa suggests that these derivatives retard plant growth by inhibition of an enzyme system associated with a growth process. Electron withdrawing groups on the benzene ring, such as nitro and cyano, caused inactivation. A chloro group at 2 or 4 produced more activity than substitution at position 3. Monobromo and monomethyl derivatives substituted at 2 and 3 were equally active, while substitution at C-4 approximately doubled activity. The disubstituted chloro and methyl benzyl compounds were all highly active, regardless of the positions of these groupings.he ability of certain quaternary ammonium compounds to reduce stem elongation of bean plants without caus-T ing abnormal, formative changes was first reported by Mitchell et al. (1949). One of the most active compounds was a quaternary ammonium carbamate, designated Amo-1618(4-hydroxyl-5-isopropyl -2 -methylphenyltrimethylatnmonium chloride, 1-piperidine carboxylate), prepared from the terpene thymol by R. L. Shriner at the University of Illinois. Much work has been done on the synthesis and testing of derivatives ofAmo-l618 (Krewson et al., 1959). Knight et al. (1969) have studied the influence on plant growth-retardant activity of various substituents of aryl quaternary ammonium, phosfonium, and sulfonium compounds. 3-Chloro-and 4-chloro-benzyltributyl ammonium bromides were the most active compounds.The plant growth-retardant activity of six benzyl quaternary ammonium derivatives synthesized from the terpene (+)-limonene, found abundantly in citrus peel oil, has been reported (Newhall and Pieringer, 1966). The effect of chain length in n-alkyl quaternary ammonium derivatives of (+)-limonene on plant growth has also been studied (Pieringer and Newhall, 1968). Two additional benzyl quaternary ammonium compounds, prepared from (+)-limonene, have been reported (Newhall and Pieringer, 1969), and their effect on the growth of citrus described (Pieringer and Newhall, 1970).All of these limonene derivatives have somewhat different structural requirements for plant growth-retardant activity than other known growth regulants. A highly significant correlation between the plant growth-retardant activities of Florida Citrus Experiment Station, IFAS, Lake Alfred, Fla. 33850 these compounds and their ability to function as inhibitors of human blood serum (pseudo) cholinesterase has been demonstrated (Newhall, 1969).In the present study, 18 additional, new, substituted benzyl quaternary ammonium derivatives of (+)-limonene were synthesized both to det...

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“…This mixture was applied as a 3-to 5-mm. band around the stem below the second node (Krewson et al, 1959;Newhall and Pieringer, 1966). Treated plants were grown for 7 days, and the lengths of the second internodes were recorded.…”

Section: Methods and Proceduresmentioning

confidence: 99%