N-butoxymethyl-2-chloro-2',6'-diethylacetanilide

N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide

C₁₇H₂₆ClNO₂

Light yellow to purple liquid with a faint, sweet odour.

-2.8 ℃ to 1.7 ℃

156  ℃/0.5 mmHg

2.4 ×10-1 mPa (25 ℃)

>135 ℃ (Tag closed cup)

1.076 (25 ℃)

In water 20 mg/l (20 ℃). Soluble in most organic solvents, including diethyl ether, acetone, benzene, ethanol, ethyl acetate, and hexane.

Decomposes at ≥65 ℃. Stable to u.v. light. Stable indefinitely ≤45 ℃.

3.74 ×10^-3 Pa m³

Inhibits cell division by blocking protein synthesis; more recent research suggests chloroacetamides may inhibit synthesis of very long chain fatty acids.

Selective systemic herbicide, absorbed primarily by the germinating shoots, and secondarily by the roots, with translocation throughout the plant, giving higher concentrations in vegetative parts than in reproductive parts.

Used pre-emergence for the control of annual grasses and certain broad-leaved weeds in rice, both seeded and transplanted. It shows selectivity in barley, cotton, peanuts, sugar beet, wheat and several brassica crops. Effective rates range from 1.0-4.5 kg/ha. Activity is dependent on water availability such as rainfall following treatment, overhead irrigation or applications to standing water as in rice culture.

Non-phytotoxic to rice, cotton, barley, wheat, peanuts, sugar beet, and some brassicas.

Acute oral LD₅₀ for rats 2000, mice 4747, rabbits >5010 mg/kg.

Acute percutaneous LD₅₀ for rabbits >13 000 mg/kg. Moderate skin irritant; practically non-irritating to eyes (rabbits). Contact sensitisation reactions observed in guinea pigs.

LC₅₀ (4 h) for rats >3.34 mg/l air.

For rats 100 mg/kg diet (ppm), for mice 50 mg/kg diet (ppm), for dogs 5 mg/kg b.w. daily.

WHO (a.i.) U; EPA (formulation) III

Acute oral LD₅₀ for mallard ducks >4640 mg/kg. Dietary LC₅₀ (5 d) for mallard ducks >10 000, bobwhite quail 6597 mg/kg diet.

LC₅₀ (96 h) for rainbow trout 0.52, bluegill sunfish 0.44, carp 0.32, channel catfish 0.10-0.14, fathead minnow 0.31 mg/l.

LC₅₀ (48 h) 2.4 mg/l.

Rapidly metabolised in plants to water-soluble metabolites, leading eventually to mineralisation.

Metabolised to water-soluble metabolites and excreted.

In soil, degradation is principally by microbial activity (Y.-L. Chen and T.-C. Wu, Nippon Noyaku Gakkaishi, 1978, 3, 411). Persists for c. 6-10 weeks. Converted in soil or water to water-soluble derivatives, with a slow evolution of CO₂.

analysis by glc with FID (AOAC Methods, 17th Ed., 986.04; CIPAC Handbook, 1988, D, 17) or by i.r. spectrometry.