Chlordimeform

Crowder LA, Whitson RS. 1980. Fate of toxaphene, methyl parathion, and chlordimeform combinations in the mouse. Bull Environ Contam Toxicol 24 444-451. 

Chloroformanilide, see 4-Chloroaniline, Monuron p -Chloro-o-formotoluidide, see Chlordimeform 4-Chloro-2-formylphenol, see MCPA Chlorohydrin, see 2-Chloroethyl vinyl ether Chlorohydroquinone, see Chlorobenzene, 2-... 

Chlorotoluene, see Toluene 4 -Chloro-o-toluidine, see Chlornhenamldlne. Chlordimeform... 

Witkonton and Ercegovich (1972) studied the transformation of chlordimeform in six different fruits following foliar spray application. They found //-chloro-o-formotoluidide was the only major metabolite identified in apples, pears, cherries, plums, strawberries, and peaches. Chemical/Physical. Reacts with acids forming soluble salts (Hartley and Kidd, 1987). 

Competitive adsorption on clay and soils surfaces between a heavy metal contaminant (Cu) and a cationic herbicide (chlordimeform) was reported by Maqueda... 

There is evidence to indicate that chlordimeform [ N -(4-chloro- -toly1)-IJ, -dimethyIformamidine] requires metabolic activation to demethylchlordimeform (DCDM) and that it is DCDM which is responsible for the behavioral and toxicological properties of chlordimeform (20). 

Support for this is found in the substantially greater octopa-minomimetic activity of DCDM compared to chlordimeform (20) and the observation that mixed function oxidase inhibitors, e.g. piperonyl butoxide and sesamex, strongly antagonized the toxicity of chlordimeform to the southern cattle tick larvae and synergized the toxicity of DCDM (21). Therefore, chlordimeform may be considered to be a propesticide of DCDM. 

Needless to say, it would be interesting to apply the same type of chemistry described in Figure 2 for the methylcarbamate esters to the synthesis of derivatives of the formamidine insecticides. However, additional work with the formamidines, particularly those related to chlordimeform, has been discouraged because of the mutagenic and carcinogenic potential of the aryla-mine metabolic products. 

Figure 1. Structures of octopamine, norepinephrine, the pesticide/pestistat chlordimeform (CDM), and related compounds.

Chloro-ort/2o-toluidine is a major metabolite of chlordimeform and it has been detected in the urine of workers exposed to chlordimeform in packaging and agriculture (Folland etal., 1978 Geyer Fattal, 1987). Exposure to 4-chloro-ort/2o-toluidine and chlordimeform were measured in the urine of chlordimeform production workers and was reported to be minimal after substantial improvement of working conditions in a chlordimeform-manufacturing plant in 1980 (Popp et al., 1992). Stasik (1991) reported that 4-chloro-ort/io-toluidine was detected in the urine of two workers at a chemical plant 12 and 24 h after exposure at concentrations of 1.7 and 2.1 mg/L, respectively. 

Chloro-ort/20-toluidine occurred in water as a result of the hydrolysis of chlordimeform via hydrolysis of the intermediate N-formyl-4-chloro-ort/7o-toluidine (WHO, 1998). 

The microbial degradation of chlordimeform in soils by a number of bacterial and fungal species has led to formation of 4-chloro-ort/zo-toluidine (Johnson Knowles, 1970). When C-labelled 4-chloro-ort/2o-toluidine was incubated at a concentration of 5 ppm [mg/kg] in non-autoclaved soil, almost 20% of 4-chloro-ort/2o-toluidine was metabolized to carbon dioxide within 40 days (Bollag et al., 1978). 

Chloro-ort/2o-toluidine has been identified in field samples of plant materials treated with chlordimeform, e.g., in young bean leaves at concentrations of less than 0.1-0.2 ppm [mg/kg], in grape stems at 0.02-0.3 ppm [mg/kg], in a mixture of grape stems and berries at 0.02-0.5 ppm [mg/kg] and in prunes and apples at less than 0.04 ppm [mg/kg] (Kossmann et al., 1971). In an experimental field application (one to three treatments with chlordimeform, harvesting 42 days after last treatment), 4-chloro-ort/zo-toluidine was found in rice grains at 3-61 ppb [ Xg/kg] and in straw parts at 80-7200 ppb [pg/kg] (lizuka Masuda, 1979). 4-Chloro-ort/70-toluidine was detected as a metabolic product in cotton plants following treatment with chlordimeform (Bull, 1973). 

Chloro-ort/2o-toluidine and its hydrochloride salt were produced commercially in substantial amounts as intermediates in the manufacture of azo dyes and chlordimeform, an insecticide. Since the 1980s, production and use of 4-chloro-ort/20-toluidine have been discontinued in most countries. 

Three small cohort studies of workers exposed to 4-chloro-ort/2o-toluidine, one each among dye, 4-chloro-ort/70-toluidine and chlordimeform production workers, were... 

Geyer, R. Fattal, F. (1987) HPLC determination of the metabolite 4-chloro-o-toluidine in the urine of workers occupationally exposed to chlordimeform. J. anal. Toxicol., 11, 24-26 Goggelmarm, W, Bauchinger, M., Kulka, U. Schmid, E. (1996) Genotoxicity of 4-chloro-o-toluidine in Salmonella typhimurium, human lymphocytes and V79 cells. Mutat. Res., 370, 39-47... 

Leslie, C., Reidy, G.F., Murray, M. Stacey, N.H. (1988) Induction of xenobiotic biotransfor-mationby the insecticide chlordimeform, a metabolite 4-chloro-o-toluidine and a stracturally related chemical o-toluidine. Biochem. Pharmacol, 37, 2529-2535 Lewis, R.J., Jr (1993) Hawley s Condensed Chemical Dictionary, 12th Ed., New York, Van Nostrand Reinhold, p. 55... 

Popp, W., Schmieding, W., Speck, M., Vahrenholz, C. Norpoth, K. (1992) Incidence of bladder cancer in a cohort of workers exposed to 4-chloro-orf/ o-toluidine while synthesizing chlordimeform. Br. J. ind. Med., 49, 529-531... 

Control of cattle ticks has followed a similar transition from broad spectrum organophosphates to more selective agents with novel mode of action. In 1956 diazinon (81) was introduced into Australia as the first organophosphate for tick control. Evidence of OP resistance was first detected in 1963 and in 1966 chlordimeform (84) was demonstrated to control the OP-resistant strains. 

This new compound was the prototype for several series. From this original structure were developed amitraz (85), chlormethiuron (86), cymiazole (87) and clenpyrin (88), all of which have been used to control OP-resistant strains of B. microplus. Chlordimeform (84) was later withdrawn from sale and amitraz (85) became the market leader. There is... 

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