Bromoxynil octanoate

Country Effective Date Description of action taken Grounds for decision 

NOR 2000 The chemical is banned. It is prohibited to import, sell and use bromoxynil as a pesticide. Extremely toxic to aquatic organisms. (Reference (EP3) UNEP/FAO - PIC Circulars XIV, XV, XVI, XVII - 12/2001,6/2002. 12/2002,6/2003, ) 

Scientific and common names, and synonyms ARSENIC ACID (H3ASO4), CALCIUM SALT (2 3) ARSENIC ACID, CALCIUM SALT (2 3)  

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Boron oxide Bioaerosol Bitumen fume Bromotrifluoro methane Bromoxynil Bromoxynil octanoate Butadiene (1,3-butadiene)... 

In those cases where the total residue in not represented by a single marker compound, a more complex residue definition is necessary. The hydrolytically unstable ester of bromoxynil octanoate is presented as an example here (Table 1). 

Bromoxylenol blue, 4 362t Bromoxynil, 4 358t 13 315 crop resistance to, 13 360-361 Bromoxynil octanoate, 4 358t 2-(Bromozincio)-3-alkyl-5-bromothiophene, 7 518... 

Bromoxynil octanoate 2,6-dibromo-4-cyanophenyl octanoate C15H17Br2N02 403.109 45 16 0.629 4.08 ... 

Brown, D.F., McDonough, L.M., McCool, D.K., Papendick, R.I. (1984) High performance liquid chromatographic determination of bromoxynil octanoate and metribuzin in runoff water from wheat fields. J. Agric. Food Chem. 32, 195-200. 

Ioxynil and bromoxynil can be easily esterified with add chlorides ydth longer carbon atom chains. Thus, esterified with octanoyl chloride, ioxynil octanoate and bromoxynil octanoate are formed. These derivatives are readily soluble in xylene (SOO and 400 g/1 resp.), and are thus, suitable for the preparation of emulsifiable concentration formulations (Totril, 250 g ioxynil/1) and Brominal , 240 g active ingredient/1. In the plants the esters are degraded to the parent herbidde and exert their action in this form. 

Bromoxynil is a special case because the parent compound bromoxynil-octanoate, although being a baseline toxicant, is highly toxic due to its high hydrophobicity (Fig. 10). The hydrolysis product bromoxynil is the active ingredient and has a specific mode of action Bromoxynil is a potent inhibitor of Photosystem II and is also an uncoupler of photophosphorylation (i.e. destroys the electrochemical proton gradient formed in the electron transport... 

According to the calculations of Gasser et al. [41] the presence of bromoxynil-octanoate in water is negligible. Also, despite its high specific toxicity bromoxynil does not dominate the toxic potential because its fraction is only 6% (Fig. 11). Instead, the metabolites B-benzamide and B-benzoic acid are the dominant species and also contribute most to the toxic potential of the mixture. However, their mode of action is not defined and therefore the uncertainty in our predictions is large. 

Smith, A.E. An Analytical Procedure for Bromoxynil and Its Octanoate in Soils Persistence Studies with Bromoxynil Octanoate in Combination with other Herbicides in... 

DI3325000 Bromoxynil octanoate K10875000 Di-n-butyl phthalate... 

Dibromo-4-octanoyloxybenzonitrile, see Bromoxynil octanoate Dibutyl-1,2-benzenedicarboxylate, see Di- -butyl phthalate Dibutyl phthalate, see Di- -butyl phthalate... 

Bromoxynil octanoate (Octanoic acid, 2,6-dibromo-4-cyanophenyl ester) (CAS No. 001689-99-2)... 

Brickley, M. R. Lawrie, F. Weise, V. Hawes, C. Cobb, A. H. Use of a potentiometric vital dye to determine the effect of the herbicide bromoxynil octanoate on mitochondrial bioenenergetics in Chlamydomonas reinhardtii. Pest Manag. Sci. 2012, 68, 580-586. 

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