1441. Bromoxynil

Nomenclature

CAS number: 1689-84-5
3,5-Dibromo-4-hydroxybenzonitrile; 3,5-dibromo-4-hydroxyphenyl cyanide; 2,6-dibromo-4-cyanophenol; broxynil; ENT-20852; MB-10064.
C7H3Br2NO; mol wt 276.91.
C 30.36%, H 1.09%, Br 57.71%, N 5.06%, O 5.78%.

Description and references

Selective contact herbicide. Prepn: K. Auwers, J. Reis, Ber. 29, 2359 (1896); E. Müller et al., Ber. 92, 2278 (1959); K. Carpenter et al., Weed Res. 4, 175 (1964); FR 1375311 (1964 to May & Baker), C.A. 62, 3982h (1965). Herbicidal activity: K. Carpenter, B. J. Heywood, Nature 200, 28 (1963). HPLC analysis: J. C. Van Damme, M. Galoux, J. Chromatogr. 190, 401 (1980). Persistence in soil: A. E. Smith, Pestic. Sci. 11, 341 (1980).

Chemical structure

Properties

Colorless solid, mp 194-195°. pKa 4.06. Subl at 135° (0.15 mm Hg). Slightly volatile in steam. Soly in (g/l) at 25°: water 0.13; methanol 90; acetone 170; tetrahydrofuran 410. LD50 orally in mice: 111 mg/kg (Carpenter, 1964).

Derivative

Octanoate.

Nomenclature

CAS number: 1689-99-2
MB-10731; NPH-1320; RP-16272; Brominal (Bayer CropSci.); Buctril (Bayer CropSci.).
C15H17Br2NO2; mol wt 403.11.
C 44.69%, H 4.25%, Br 39.64%, N 3.47%, O 7.94%.

Properties

Waxy solid, mp 45-46°. Low volatility; subl at 90° (0.1 mm Hg). Insol in water.

Use

Herbicide.