Plant Growth Regulators, Synthesis and Preliminary Evaluations of Amide, Lactic Acid, and Terpenoid Derivatives of Substituted Phenoxycarboxylic Acids

Krewson, C. F.; Saggese, E. J.; Carmichael, J. F.; Ard, J. S.; Drake, T. F.; Mitchell, J. W.; Smale, B. C.

doi:10.1021/jf60096a006

Cited by 10 publications

(7 citation statements)

References 4 publications

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“…Galacturonic acid has the function of plant growth regulation and defense against pathogens, since the galacturonic acid acts as a critical component of pectins in plant cell walls (Kovensky et al ; Kuivanen et al ). Lactic acid was mainly implicated in glycolysis and ATP synthesis in plants and its polymers and derivatives were found as important growth regulators under optimum and drought conditions (Krewson et al ; Xu et al ). The accumulation of lactic acid was also suggested to be related to ABA‐ and GABA‐enhanced OA in creeping bentgrass under drought stress (Li et al ).…”

Section: Discussionmentioning

confidence: 99%

Nitric oxide, γ‐aminobutyric acid, and mannose pretreatment influence metabolic profiles in white clover under water stress

Zhou

Yong

Cheng

et al. 2019

JIPB

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Nitric oxide (NO), γ‐aminobutyric acid (GABA), and mannose (MAS) could be important regulators of plant growth and adaptation to water stress. The application of sodium nitroprusside (SNP, a NO donor), GABA, and MAS improved plant growth under water‐sufficient conditions and effectively mitigated water stress damage to white clover. The metabonomic analysis showed that both SNP and GABA application resulted in a significant increase in myo‐inositol content; the accumulation of mannose was commonly regulated by SNP and MAS; GABA and MAS induced the accumulation of aspartic acid, quinic acid, trehalose, and glycerol under water deficit. In addition, citric acid was uniquely up‐regulated by SNP associated with tricarboxylic acid (TCA) cycle under water stress. GABA specially induced the accumulation of GABA, glycine, methionine, and aconitic acid related to GABA shunt, amino acids metabolism, and TCA cycle in response to water stress. MAS uniquely enhanced the accumulation of asparagine, galactose, and D‐pinitol in association with amino acids and sugars metabolism under water stress. SNP‐, GABA‐, and MAS‐induced changes of metabolic profiles and associated metabolic pathways could contribute to enhanced stress tolerance via involvement in the TCA cycle for energy supply, osmotic adjustment, antioxidant defense, and signal transduction for stress defense in white clover.

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Section: Discussionmentioning

confidence: 99%

Nitric oxide, γ‐aminobutyric acid, and mannose pretreatment influence metabolic profiles in white clover under water stress

Zhou

Yong

Cheng

et al. 2019

JIPB

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“…Furthermore, some substituted aryloxyacetic acid derivatives also exhibit good plant growth‐regulating activity(12). However, unfavorable responses occurred in a few cases; for instance, suppression of leaf growth was observed (13) when the substituted aryloxyacetic acids were used to improve fruit set. Therefore, seeking highly active and effective agents remains a sufficient room.…”

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confidence: 99%

Design, Synthesis, Biological Activities, and 3D‐QSAR of New N,N′‐Diacylhydrazines Containing 2‐(2,4‐dichlorophenoxy)propane Moiety

Liu

et al. 2011

Chem Biol Drug Des

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A series of new N,N'-diacylhydrazine derivatives were synthesized efficiently under microwave irradiation. Their structures were characterized by (1) H NMR, MS, and elemental analysis. Various biological activities of these compounds were tested. Most of them exhibited higher herbicidal activities against dicotyledonous weeds than monocotyledonous weeds. In addition, favorable in vivo fungicidal activities were also found of these compounds against Cladosporium cucumerinum, Corynespora cassiicola, Sclerotinia sclerotiorum(Lib.)de Bary, Erysiphe cichoracearum, and Colletotrichum orbiculare (Berk aLMont) Arx. All compounds displayed excellent plant growth regulatory activities: 100% inhibition was achieved against the radicle growth of cucumber. To further investigate the structure-activity relationship, comparative molecular field analysis was performed on the basis of herbicidal activity data, resulting in a statistically reliable model with good predictive power (r(2) = 0.913, q(2) =0.556). Based on the calculation, five additional novel compounds were designed and synthesized. Satisfyingly, compound 4u displayed excellent herbicidal activity (94.7%) at 1500 g/ha, although it is less active than 2,4-D. Meanwhile, this compound also exhibited good fungicidal activity against C. orbiculare (Berk aLMont) Arx (82.16%).

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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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Plant Growth Regulators, Synthesis and Preliminary Evaluations of Amide, Lactic Acid, and Terpenoid Derivatives of Substituted Phenoxycarboxylic Acids

Cited by 10 publications

References 4 publications

Nitric oxide, γ‐aminobutyric acid, and mannose pretreatment influence metabolic profiles in white clover under water stress

Nitric oxide, γ‐aminobutyric acid, and mannose pretreatment influence metabolic profiles in white clover under water stress

Design, Synthesis, Biological Activities, and 3D‐QSAR of New N,N′‐Diacylhydrazines Containing 2‐(2,4‐dichlorophenoxy)propane Moiety

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

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