1- naphthylphthalamic acid

Naphthyloxy)ethanol [93-20-9] M 188.2, m 76.7". Crystd from benzene/pet ether. 7V-1-Naphthylphthalamic acid [132-66-1] M 291.3, m 203". Crystd from EtOH. 

Another area in which Arabidopsis genetics is proving to be useful is the study of the proposed role of flavonoids in regulating auxin transport. Several years ago, Jacobs and Rubery published the first evidence that flavonoids could specifically compete with naphthylphthalamic acid for binding to the auxin efflux carrier in etiolated zucchini hypocotyls.35 This finding was somewhat controversial, however, and no additional evidence for the connection between flavonoids and auxin transport was reported for some time. Brown et al. have now used Arabidopsis flavonoid mutants to generate new evidence in support of a role for flavonoids in the regulation of polar auxin movement.6 These experiments took... 

Af-1-naphthylphthalamic acid org chem C oH7NffCOC6H4COOtf A crystalline solid with a melting point of 185 C used as a preemergence herbicide. en wan naf-thil-tha Iam-ik as-ad ... 

Murphy AS, Hoogner KR, Peer WA, Taiz L. 2002. Identification, purification, and molecular cloning of N-l-naphthylphthalamic acid-binding plasma membrane-associated aminopeptidases from Arabidopsis. Plant Physiol 128 935-950. 

Orf/zo-alkylated anilines, such as 2-methyl-6-ethylaniline (96), and 2,6-diethylaniline (97), are used in the production of acetanil-like pre-emergence herbicides, applied to corn, soyabeen, etc. The amine 97 is the starting point for the selective systemic alachlor (98) (Scheme 21). Acylation of 38 with phthalic anhydride affords the pre-emergence herbicide naptalam (AM-naphthylphthalamic acid) (99). 

Hoffman and Smith (1949a) reported in the plant growth activity of N-aryl-phthalamic acids. The only one used as a herbicide is N-l-naphthylphthalamic acid (naptalam, 33). 

Phytotropins are synthetic molecules which affect the tropic responses, inhibit auxin transport and bind to the receptor for 1-N-naphthylphthalamic acid (NPA) (10-1) [91-93]. For a recent review see [94]. A simple assay to detect and compare activities is measurement of antigravitropic activity on cress seedlings [95]. There are two phytotropin recognition sites on the NPA receptor, or two receptors, which recognize phytotropins... 

Fig. 2. MTs in cells of ev. Alarik maize roots after their treatments either with the auxin transport inhibitor naphthylphthalamic acid (NPA) (100 pM, 6 h) (a-g) and with lAA (100 pM, 24 h) (h-j). After NPA treatment, periclinal divisions were induced in the outer cortex (a, thin arrows indicate young cell walls, thick arrow indicates pre-prophase band of MTs). Cells of the epidermis preserved well-ordered transverse CMTs both near the root apex (b) and in the transition zone (g). On the other hand, cells of the root cap (c), outer cortex (d), inner cortex (e) and of the stele parenchyma (f) showed disturbances to their general appearance and ordering (compare with Figs. 3c, d, g, h). Similarly to NPA treatment, relatively well-ordered transverse CMT arrays are still preserved in postmitotic cells of the epidermis (h) as well as in all cells of the former meristem (i,j) after the auxin treatment. Abbreviations EP, epidermis IC, inner cortex OC, outer cortex RC, root cap.

The process of auxin transport can be inhibited by a group of synthetic compounds which bind to a specific cell membrane receptor. Several flavonoids, including quercetin (7), apigenin (5), and kaempferol (6), can specifically compete with one of the synthetic compounds, naphthylphthalamic acid, at micromolar levels for binding to the receptor and, thereby, perturb auxin transport in a variety of plant tissues (Jacobs and Rubery, 1988). Although quercetin (7) was highly active, a common quercetin glycoside, rutin (35) proved inactive. 

Synonyms ACP 322 Alanap Alanap L Alanape Alanap lOG AT Dyanap Morcran 2-((l-Naphthalenylamino)carbonyl)benzoic acid a-Naphthylphthalamic acid A-l-Naph-thylphthalamic acid Naptalame Nip-A-Thin NPA PA Peach-Thin 6Q8 Solo. 

Abbreviations ABA = abscisic acid 2,4-D = 2,4-dichlorophenoxyacetic acid DNP = 2,4-dinitrophenol GA3 = gibberellic acid IAA = indole-3-acetic acid IB A = indole-3-butyric acid NAA = naphthalene-1-acetic acid NPA = naphthylphthalamic acid PEP = phos-phoenolpyruvate 2,3,5-T = 2,3,5-trichlorophenoxyacetic acid TIBA = 2,3,5-triiodoben-zoic acid. 

Specificity of the Auxin Transport System. Comparative studies with chemically closely related compounds reveal a positive correlation between auxin activity and degree of basipetal polarity in the transport of these substances (e.g.. Went and White 1939, Leopold and Lam 1961, Jacobs 1967, Hertel etal. 1969, Veen 1972). Further, the basipetal transport of auxins is specifically inhibited by substances such as TIBA, naphthylphthalamic acid (NPA), 3,3a-dihydro-2-(p-methoxyphenyl)-8H-pyrazolo[5,la] isoindol-8-one (DPX 1840) (see Sect. 3.3.4.3) not only in treated sections but also when they are applied to intact plants at the loci of natural auxin production (see p 100). In summary, the numerous transport studies make certain the presence of a unique transport system, which is specific for auxin molecules, and which moves the hormone basipetally from the natural auxin sources in the shoot and then on to the root to regulate growth and other developmental processes. It is clear that this system is fully functional in tissue sections which is the material which has been used most in transport studies. 

Lavender DP, Sweet GB, Zaerr JB, Hermann RK (1973) Spring shoot growth in Douglas-flr may be initiated by gibberellins exported from the roots. Science 182 838-839 Lembi CA, Morre DJ, Thomson KSt, Hertel R (1971) 1-N-naphthylphthalamic-acid (NPA)-binding activity of a plasma membrane-rich fraction from maize coleoptiles. Planta 99 37-45... 

Mitchell EK, Davies PJ (1975) Evidence for three different systems of movement of indoleacetic acid in intact roots of Phaseolus coccineus. Physiol Plant 33 290-294 Mitchinson GJ (1980) The dynamics of auxin transport. Proc R Soc Lond B 209 489-511 Mittelheuser CJ, van Steveninck RFM (1971) Rapid action of abscisic acid on photosynthesis and stomatal resistance. Planta 97 83-86 Morath M (1972) Some early effects of auxin and of geotropic exposure on coleoptiles. In Kaldewey H, Vardar Y (eds) Hormonal regulation in plant growth and development. Verlag Chemie, Weinheim, pp 377-381 Morgan DG (1964) Influence of a-naphthylphthalamic acid on the movement of indolyl-3-acetic acid in plants. Nature 201 476-477... 

Thomson KSt, Hertel R, Muller S, Tavares JE (1973) 1-N-naphthylphthalamic acid and 2,3,5-triiodobenzoic acid In vitro binding to particulate cell fractions and action on auxin transport in corn coleoptiles. Planta 109 337-352 Thornton RM, Thimann KV (1967) Transient effects of light on auxin transport in the Avena coleoptile. Plant Physiol 42 247-257 Tsurumi S, Ohwaki Y (1978) Transport of " C-labeled indoleacetic acid in Vicia root segments. Plant Cell Physiol 19 1195-1206... 

Thomson K-S, Hertel R, Muller S (1973) 1-N-naphthylphthalamic acid and 2,3,5-triiodo-benzoic acid In-vitro binding to particulate cell fractions and action on auxin transport in corn coleoptiles. Planta 109 337-352... 

Some flavonoids are known to share the binding sites of an artificial inhibitor [naphthylphthalamic acid (NPA)] of auxin transport in plant tissues. Such process confers... 

N-1-naphthylphthalamic acid org chem C10H7NHCOC6H4COOH A crystalline solid... 

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