Dibromo-3-Chloropropane DBCP

MacFarland RT, Gandolfi AJ, Sipes IG. 1984. Extra hepatic reduced GSH-dependent metabolism of 1,2-dibromoethane and 1,2-dibromo-3-chloropropane (DBCP) in the rat and mouse. Drug Chem Toxicol 7 213- 227. 

Soil core data are available for only six of the pesticides discussed in this paper. The six pesticides are aldlcarb atrazlne 1,2-dibromo-3-chloropropane (DBCP) 1,2-dlchloropro-pane (DCP) 1,2-dlbromoethane (EDB) and slmazlne. Cores were always sampled at depths greater than one meter and the soil was characterized physically and chemically. The importance of soil core sampling in pesticide leaching assessments is presented in the Discussion section. 

Toxicology. 1,2-Dibromo-3-chloropropane (DBCP) is a mild central nervous system depressant and causes sterility in male workers due to a selective effect on seminiferous tubules. 

Department of Labor Emergency temporary standard for occupational exposure to 1,2 dibromo-3-chloropropane (DBCP). Fed Reg 42 45535, 1977... 

Generoso, W.M., Cain, K.T. Hughes, L.A. (1985) Tests for dominant-lethal effects of 1,2-dibromo-3-chloropropane (DBCP) in male and female mice. Mutat. Res.. 156, 103-108 George, E., Wootton, A.K. Gatehouse, D.G. (1990) Mieronueleus induction by azobenzene and... 

Emergency Temporary Standard for Occupational Exposure to 1,2-Dibromo-3-chloropropane (DBCP) Hearing. Federal Register 1977, 42 (175), 45536-45543. 

While both industrial and agricultural chemicals have been found in California ground waters, pesticides injected beneath the soil surface to control nematodes are a particular concern. The nematicide 1,2-dibromo-3-chloropropane (DBCP), which was banned in California in 1977, is the most serious example of this problem in California (1-2). Figure 1 shows the increase between 1979 and 1984 in the number of wells found to contain measurable quantities of DBCP. As of April 1984, 2522 wells contained DBCP, with over half these wells (1455) having concentrations in excess of 1.0 part per billion, the current California "action level". 

As with nucleophilic substitution reactions, rates of dehydrohalogenation reactions will be dependent on the strength of the C-X bond being broken in the elimination process. Accordingly, it is expected that the ease of elimination of X will follow the series Br>Cl>F. The relative reactivities of Br and Cl toward elimination is evident from the hydrolysis product studies of 1,2-dibromo-3-chloropropane (DBCP Burlinson et al., 1982). DBCP has been used widely in this country as a soil fumigant for nematode control and has been detected in groundwaters (Mason et al., 1981) and subsoils (Nelson, et al., 1981). Hydrolysis kinetic studies demonstrated that the hydrolysis of DBCP is first order both in DBCP and hydroxide ion concentration above pH 7. Below pH 7, hydrolysis occurs via neutral hydrolysis however, the base-catalyzed reaction will contribute to the overall rate of hydrolysis as low as pH 5. Product studies performed at pH 9 indicate that transformation of DBCP occurs initially by E2 elimination of HBr and HCl (Figure 2.4). 

Reproductive Effects. Another clinical study, this one designed to assess reproductive function, involved a fumigant, 1, 2-dibromo-3 chloropropane (DBCP). In 1977, Whorton and Milby investigated the testicular function of 145 employees of a plant which formulated DBCP. They used a questionnaire, physical examination which focused on the reproductive system, sperm counts and blood tests to determine the level of the hormones that stimulate and maintain sperm production. 

Holme JA, Soderlund EJ, li M et al. Prevention of 1,2-dibromo-3-chloropropane (DBCP)-induced kidney necrosis and testicular atrophy by 3-aminobenzamide. Toxicol Applied Pharmacol 1991 110 118-128. 

Dibromo-3-chloropropane (DBCP) ( Nemagon ) and 1,2-dibromoethane are volatile nematocide formerly used to rid soil of these undesirable worms. Plants are remarkably tolerant to them but they are toxic to humans. 

Synonyms 1,2-dibromo-3-chloropropane DBCP, Fumazone Nemafume Nemagon Nemaset BBC 12 OS 1879. DBCP is also included in agricultural pesticides and... 

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