1-Naphthaleneacetamide

Description

1-naphthylacetamide is a synthetic auxin plant growth regulator used to increase fruit yield, increase fruit thinning and for striking cuttings. It is moderately soluble in water, has a low volatility and tends not to be persistent in soil or aquatic systems. The risk of leaching to groundwater is low. It has a low to moderate toxicity to biodiversity. 1-naphthylacetamide has a moderate oral toxicity to mammals and is a reproduction/developmental toxin.

Chemical Properties

white to cream powder

Uses

1-Naphthylacetamide (cas# 86-86-2) is a compound useful in organic synthesis.

Definition

ChEBI: 1-naphthaleneacetamide is a member of the class of naphthalenes that is naphthalene which is substituted by a 2-amino-2-oxoethyl group at position 1. It is a synthetic auxin that is widely used in agriculture to promote the growth of numerous fruits, for root cuttings and as a fruit thinning agent. It has a role as a synthetic auxin. It is a member of naphthalenes and a primary carboxamide.

Agricultural Uses

Plant growth regulator: 1-Naphthaleneacetamide is an agent for thinning fruit sets in apples and pear. Not currently registered for use in EU countries (pending). Registered for use in the U.S.

Trade name

AMACTONE®; AMID-THIN W®; FRUITONE®; ROOTONE® (component, with Indole-3-butyric acid and 1-Naphthaleneacetic acid); ROSETONE®; TRANSPLANTONE® (component, with 1-Naphthaleneacetic acid)

Mechanism of action

Absorbed through roots, stems and leaves, demonstrates auxin-like activity

Synthesis

The general procedure for the synthesis of 1-naphthaleneacetamide from naphthalen-1-ylacetyl chloride was as follows: 1-naphthaleneacetic acid (93.5 mg, 0.50 mmol) was dissolved in dichloromethane (0.8 mL), a catalytic amount of DMF was added, followed by the slow, dropwise addition of oxalyl chloride (135.6 mg, 1.00 mmol, 2.00 equiv.) under stirring. The reaction mixture was stirred at room temperature for 15 minutes. Upon completion of the reaction, the solution was concentrated under vacuum and the resulting residue was dissolved in tetrahydrofuran (0.8 mL). Ammonia (28%, 450.4 mg, 7.50 mmol, 15.0 eq.) was added to this solution at 0 °C, after which the reaction mixture was transferred to room temperature and stirred for 10 min. At the end of the reaction, the solution was concentrated in vacuum and purified by silica gel column chromatography (eluent: chloroform/methanol, 10/1, Rf = 0.50) to afford the target product 1-naphthaleneacetamide (Y-015) as a white solid in 72% yield.

References

[1] Patent: JP2015/89885, 2015, A. Location in patent: Paragraph 0146; 0147; 0162-0164
[2] Chimica e l'Industria (Milan, Italy), 1955, vol. 37, p. 857,860
[3] Bulletin de la Societe Chimique de France, 1965, p. 861 - 868
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 10, p. 3366 - 3376
[5] Chemistry Letters, 2015, vol. 44, # 5, p. 621 - 623

Pesticide Type

Plant Growth Regulator