Uses
Acaricide, insecticide.
Hazard
Questionable carcinogen.
Description
Chlordimeform in an insecticide and acaricide. It is moderately soluble in water and highly soluble in many organic solvents. It is volatile. Under normal conditions is would not be expected to leach to groundwater. It is moderately persistent in soil systems but would not be expected to persist in water systems. It is moderately toxic to mammals, a neurotoxin and has a high potential for bio-concentration. It is moderately toxic to birds and fish but less so to honeybees.
Chemical Properties
Colorless crystals. Melting point 32°C, boiling point 163-165°C (1.86 kPa), relative density 1.105 (25/4°C), refractive index 1.5885 (25°C). Vapor pressure at 20°C is 0.047 Pa. Solubility in water at 20°C is 250 ppm, and it is readily soluble in organic solvents. The commercial product is its hydrochloride solution. Pure chlordimeform hydrochloride [19750-95-9] is white crystals with a melting point of 225-227°C (decomposition) and a relative density of 1.110. It is readily soluble in water but poorly soluble in organic solvents. It is stable in acidic solutions, readily precipitates crystals in neutral solutions, and decomposes in the presence of alkali.
Production Methods
The industrial production of chlordimeform begins with the preparation of 4-chloro-2-methylaniline, which is reacted with dimethylformamide dimethyl acetal under controlled conditions to form the active ingredient: (EZ)-N′-(4-chloro-2-methylphenyl)-N,N-dimethylformamidine. This condensation reaction yields the active compound.
Mechanism of action
Broad-spectrum acaricide that appears to interfere with the amine-mediated control of nervous and endocrine systems. An antifeed agent.
Environmental Fate
Plant. Principal soil and/or plants metabolites are p-chloro-o-toluidine, N′-(4-chloroo-tolyl)-N-methylformamidine (desmethylchlorphenamidine) and N-formyl-p-chloro-otoluidine (Verschueren, 1983). p-Chloro-o-toluidine, N′-(4-chloro-o-tolyl)-N-methylformamidine (desmethylchlor phenamidine) and N-formyl-p-chloro-o-toluidine were identified
in rice grains and straws at concentrations of 3–61, 0.2–1, 10–38 and 80–6,900, 10–180,
67–500 ppb, respectively (Iizuka and Masuda, 1979).
Witkonton and Ercegovich (1972) studied the transformation of chlordimeform in six
different fruits following foliar spray application. They found 4′-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).
Emits toxic fumes of nitrogen oxides and chlorine when heated to decomposition (Sax
and Lewis, 1987).
Pesticide Type
Acaricide; Insecticide; Ovicide
